Stop Asking, Start Giving

Part 01Before you start

Chapter 01Introduction: The Seat Across the Table

I've spent most of this year in the same chair, in the same room in Toronto, asking strangers how they built what they built. Some of them run funds. Some of them are two people and a prototype. A few of them have sold companies to Google, Microsoft or NetApp, and a few of them are still trying to land their first paying customer. Every one of them came on The Sunny Ray Show, sat across the table from me, and talked live to whoever was tuned in.

This book is what I learned from those conversations. I've built it as a playbook from close to eighty tapings recorded between August and November 2026, arranged in the order you'll meet the problems: the idea, the first customers, distribution, the close, the raise, the team and, if you're lucky, the scale and the exit.

I'm writing it in my own voice, and I'm quoting my guests in theirs. When a guest's words appear in quotation marks, they're what that guest said on air, word for word. I haven't polished them into something smoother, because the rough version is the true one, and you can hear the person thinking in it.

Why I started asking

I've been in Bitcoin since 2011. Before that I spent eight years at Quanser building robotics, mechatronics and haptics systems that ended up in labs at MIT, Stanford and Georgia Tech. I've done business development at Kraken and worked at 3iQ, Canada's first regulated Bitcoin fund. I've been the founder who needs a meeting, and I've been the person on the other side of the inbox deciding whether to take one.

What I kept seeing from both sides was the same transaction. Someone wants something, so they ask for it. They ask for the meeting, the intro, the check, the pilot, the signature. The person being asked has heard the request a hundred times that week, and they've learned to protect their calendar from it.

So I flipped the seat. Instead of asking people for their time, I started inviting them to share what they know. I put the spotlight on them, asked the best questions I could, and gave them something useful when we were done: the episode, the clips, a page about their work. Do you see what changes when the first move is a gift?

What the show taught me about the ask

The difference was immediate and it was human. People who'd never answer a pitch said yes to an interview. And once we'd spent half an hour together on air, the conversation afterward wasn't cold anymore. We knew each other a little. I'd listened before I'd said a word about what I do.

The title of this book came out of that. Stop asking, start giving. It's the oldest advice there is, and I don't claim to have invented it. Aviv Frankel, who founded Shuttlebase after years as a TV journalist, put the payoff in one sentence on the show: "Some of my investors in both companies were people that I met hosting my podcast."

That line sits underneath every chapter here. Fundraising comes down to relationships with people who hold capital, closing comes down to the relationship at the moment of commitment, and your team is the set of relationships that carries the company when you can't.

How to read this book

Each chapter follows a stage of company building and draws on the guests whose stories fit it best. I've kept the guest quotes short and attributed every one of them. A full list of sources, with the episode and date behind each quote, sits at the back of the preview, so you can go listen to the full conversation if a line grabs you.

I moved the go-to-market chapter close to the front on purpose. Most books put distribution in the middle, after the product's built. My guests kept telling me the opposite: the companies that struggled had a product and no way to reach anyone, and the ones that broke through had relationships before they had a finished product. So you'll read about giving before you read about first customers, because in my experience the giving is how the first customers show up.

There's also a chapter on closing. It earned its own place. A lot of founders can open a conversation and very few can finish one, and the guests who'd closed big deals had specific, practical things to say about it.

Who this is for

I wrote this for the person who's building something and wants the shortcut that isn't a trick. Maybe you're pre-product and wondering whether your idea deserves the next ten years. Or you have revenue and no idea how to raise, or you're running a team for the first time and realizing nobody prepared you.

Whatever stage you're at, the guests in these pages have been there and said something worth underlining. I'd rather hand you their words than my summary of them.

One request before you start. As you read, keep a short list of the people you'd most like to learn from in your own market, the buyers, investors and operators you'd love ten minutes with. By the end of chapter two you'll have a way to reach them that doesn't involve asking for anything. Who's the first name on that list?

Part 02The idea

Chapter 02Idea and Conviction

Every company on the show started as a problem somebody couldn't stop thinking about. What surprised me was how rarely the problem came from a brainstorm. It came from a printer queue, a payroll that wouldn't clear, a ferry with a battery that was too big. The guests who'd built something durable could point to the moment they noticed the problem, and most of them noticed it while doing a job.

This chapter is about that moment, and about what has to be true after it for an idea to deserve years of your life.

The problem shows up at work

Graham Topol runs MGT Insurance, a carrier for small businesses. Before that he was a banker and an investor, and at one point he was inside an insurance brokerage that called itself a tech company watching the same thing happen every morning. He finally asked the CTO, in his words, "why is there a line at the printer every single day?" The answer was that insurance companies still wanted documents printed and mailed, or scanned and faxed.

He walked me through the economics of a small policy. A bakery might pay a few thousand dollars a year for coverage, and that policy could take two to four weeks and four different people to underwrite. Graham's framing of the customer has stuck with me since: "You open a bakery because you love to bake." Nobody opens a bakery to fill out insurance forms. That gap between what the customer wants to do and what the system makes them do is where his company lives.

Sebastian Serrano's story starts the same way, with a problem he had to solve for himself. In 2012 he was in San Francisco with a team of developers back in Argentina, and paying them was a nightmare. In his words, "trying to find a solution to that, like how to send money back to Argentina, is how I found Bitcoin." He started buying Bitcoin in the United States and selling it locally so the payroll could clear, and the workaround grew into Ripio.

Anders Teigland's version came out of the numbers. He studied short-haul ferries in Norway and found operators had bought batteries far bigger than the routes needed, which pushed him toward a different anode material that charges fast and costs less. He told me he'd always wanted to turn science into technology and technology into products that help people. The ferries gave him a specific place to start.

Have you written down the moment your problem first showed up, in the plainest words you can?

Technology is the easy part

Madhukar Bhatia sits on both sides of the table now. He's a partner at Pentathlon Ventures in Pune, and before that he founded an analytics company that ran for eight years before it shut down. When I asked what he'd tell his younger self, he didn't soften it. His team had been, as he put it, "so busy solving a cool tech problem" that they never worked out who'd pay for the solution.

Now when a founder pitches him, his first questions are about the market, and they're blunt: "Do you understand the market that you're going to serve, and do you have any unique insight?" He's looking for someone who knows the buyer better than the buyer's current vendor does.

Jorge Alcantara, who builds tooling for product decisions at Zentrick, said it with the bluntness of an engineer who's shipped a lot of software: "code has absolutely zero value. Software has zero value." The value shows up only when a product solves somebody's problem. I heard versions of this from builders in biotech, energy and AI. Anyone who'd lived through a failure said it with the most feeling.

Luca Pandolfi brought the same idea into deep tech. His company, Woodland Bio, commercializes wood-to-fuel technology that someone else already invented and patented. He spent a year in college studying why so many patents never reach the market, and he came out of it with a conviction he repeats often: "IP is only as good as your ability to commercialize the IP." Luca chose to be the person who carries proven science the last mile.

If you took your technology away, what would your company still have?

Conviction comes from hours

I've owned Bitcoin since 2011, and I've watched a lot of people buy it, panic and sell. Mitchell Clarke, who spends his days thinking about credit products built on Bitcoin, told me about his own first purchase in 2017. He bought without understanding it, watched it fall hard, and admitted on air that fear had kept him from understanding it because "you don't know what you don't know." In 2020 he went deep and studied the monetary case properly. His conviction since then has survived every drawdown.

That story applies well beyond Bitcoin. Conviction that comes from a hot market evaporates when the market cools. The conviction that holds comes from hours of study and contact with the problem. Mitchell's view was that if you haven't put in that time, you shouldn't hold a material amount of Bitcoin, and I'd say the same about a material share of your career.

Mick Kanfi gave me the version for builders. He runs Earth Collective, an online accelerator for impact startups, and he modelled what a traditional cohort accelerator would return. His conclusion was sobering: "you gotta be prepared to make an investment for 10 years." He rebuilt his model around a global platform instead of a physical cohort, because he'd done the math before committing.

How many hours have you spent with the people who have your problem, compared with the hours you've spent building for them?

Start before you're ready

There's a tension here, and I don't want to pretend otherwise. You need enough conviction to commit for a decade, and you can't get that conviction by thinking in a room. Sam Kamani, who hosts a podcast, invests as an angel and has two exits behind him, put the other side of it simply. You don't need to spend three years mulling an idea; in his words, "you just start and you learn on the job."

Sam's point is that most of what founders do is learnable by doing it. Timing is the thing you can't plan for, and the only way to catch good timing is to keep putting product in front of the market until something moves. He's interviewed hundreds of founders, and the ones he backs keep shipping whether the current company works or not.

Itay Kahana is a good example of an idea that came from shipping. Before he founded Watchful, he was at Any.do, and he described a stretch where his team worked weekends to improve retention by a few points while a competitor improved by far more. He couldn't see what the competitor had changed. That frustration became Watchful, which tracks what rivals ship so you're never guessing again.

Jim Donnelly, who has founded six companies and is now building preventive longevity clinics, came at conviction from somewhere personal. His father spent years in cancer treatment, and no clinician ever talked to him about nutrition or exercise. Jim watched it happen and decided to build the alternative. He also gave me a phrase I've repeated many times since: "a lack of options provides clarity." When there's only one thing you can live with doing, the decision gets easy.

What's the smallest version of your idea you could put in front of a real customer this month?

The test I use now

After all these conversations, I run every new idea through a few plain questions before I give it any more of my time.

First, did the problem show up while someone was trying to do their job, or did I imagine it? Graham's printer queue and Sebastian's payroll were real. An imagined problem gets polished in slides and never meets a customer.

Second, do I know the buyer better than their current vendor does? Madhukar's question is the one I can't get around, and it's the one his first company never answered.

Third, would I still be working on this in ten years if it grew slower than I hoped? Mick's math is a gift here. It's cheaper to face the decade on paper than to discover it halfway through.

And fourth, can I start this week? Sam's advice cuts against the other three on purpose. Use the questions to choose, and let the market tell you whether you chose well.

From here on I'll assume you've picked a problem worth the time. Your next question is how you reach the people who have it, and that's where my own approach to the show began. Before you turn the page, write down the ten people whose problem you'd most like to understand. Who are they?

Part 03Reaching people

Chapter 03Stop Asking, Start Giving

I put this chapter second on purpose. In most playbooks, distribution waits until the product's built and the first customers are in. My guests kept telling me the order runs the other way. The companies that stalled had something to sell and nobody to sell it to. The companies that moved had relationships first, and the product found its buyers through them.

This chapter is the approach I use myself, the one that gave this book its title. It starts with a simple observation about the ask, and it ends with a show of your own.

Everybody is asking

Think about the messages you got this week. One sender wants fifteen minutes and another wants an intro. A third wants feedback on a deck, which means they want money. Each message is polite, and each one asks you to give up something scarce for the sender's benefit.

I've sent plenty of those messages. When I was doing business development, I'd write the careful note about why my company mattered and then ask for the meeting. Sometimes it worked. More often it went into the pile with everyone else's careful note, because the person reading it had a hundred of them and no reason to pick mine.

What I noticed on the other side of the inbox was how fast the pattern becomes invisible. When I'm the one being asked, I'm scanning for the request, and once I find it I already know how the message ends. The sender has told me what they want from me before they've given me any reason to care about them.

So the question I started asking myself was simple. What would I say yes to, every time, from someone I'd never met?

The invitation nobody turns down

The answer I kept coming back to was an invitation to talk about my own work. When someone wants to understand what I'm building, asks thoughtful questions and puts the conversation somewhere other people can find it, I say yes. Almost everyone does. It's the one message in the inbox that gives before it asks.

That's the whole mechanism behind The Sunny Ray Show. My guests are people I admire, or people I want to understand, and they come on to talk about what they've built. Nobody gets asked for a meeting or a check or a pilot. What they get is the spotlight and my full attention for half an hour.

Aviv Frankel figured this out on his own. He'd spent time in TV journalism, then founded an ecommerce company and later Shuttlebase, which automates conversion-rate work for online stores. Along the way he hosted a podcast. When I asked what it had done for him, he said, "It put investors in front of me. Some of my investors in both companies were people that I met hosting my podcast."

Notice what Aviv didn't do. He didn't go to those investors with a deck. He invited them to a conversation as guests and listened to what they knew. The relationship grew from there. When the time came to raise, he was raising from people who already knew him.

Who would you invite onto your show tomorrow, if you had one?

Why the conversation changes

Sam Kamani has hosted hundreds of conversations with founders and investors. He told me something about the difference between a pitch and an interview that I think about every week. When a founder talks to an investor, they want to show only the good things. But, as Sam put it, "on my show they're not pitching to a VC."

That shift is where the value comes from, on both sides. A guest who isn't pitching tells you how things went, including the parts that hurt. A host who isn't pitching gets to hear it. You learn more in thirty minutes of honest conversation than in a month of polished meetings, and the person across from you leaves feeling understood rather than processed.

Hosting also forces a discipline that selling rarely does. You have to prepare. A good host asks a question and then stops talking long enough to hear the answer, and stays curious about someone else's business for the whole conversation, without steering it back to yours.

Reagan Rodriguez, who runs a business in the Miami area and gives a share of it back to his community, described the attitude well. He said that if "you take the time to talk with people and really listen," something useful will come up from that desire to help. He was talking about his neighbourhood, and it applies to every market I know.

Shikha Miglani built Saarthee, an analytics firm, for eight years without a sales team. Her explanation was close to Reagan's. She said "the most important thing you can do as a founder is to talk to your prospective customers," because they keep coming back to you with problems you can solve. A show is a way of having those conversations on purpose, at a pace you can sustain.

When did you last spend half an hour with a potential customer without mentioning your product?

Network over audience

The first objection I hear is about audience. Founders tell me they don't have one, so a show seems pointless. I understand the worry, and I think it's measuring the wrong thing.

Yaniv Feldman, who founded Flag Capital after years at Microsoft, started a technology blog in Hebrew in 2008. Everyone told him nobody would read it. He did it anyway, and his reason is the one I'd give you: "I'm not looking for the audience. I'm looking for, you know, to build a network." He judged the blog by the people it connected him with, and that's the test I'd suggest for any show you start.

I measure my own show the same way. Some episodes reach a lot of people, and some barely get watched. I'm happy with both, because the person I most wanted to reach was the guest, and the guest showed up. The episode is a record of a conversation that already did its job. Anyone else who watches is a bonus.

Tim Hayden, who founded Brain+Trust and spent years in experiential marketing, was talking about how brands earn a place in memory through taste, sound and the feel of a store when he said, "It almost always starts offline." I think the same holds for relationships. A live conversation with a real person, even a video call, is the closest most of us get to offline at scale. You're two people talking, and nobody's reading a script.

If the guest were the only person who ever watched an episode, would it still be worth recording?

Giving after the taping

The giving doesn't stop when the recording does. I've learned that the half hour after a taping matters as much as the half hour during it.

When we wrap, I thank the guest on air and stay on for a minute after the stream ends. Then I send them everything they'd want to share: the video links, a page about the episode, short clips and a thumbnail. If the guest has a better photo of themselves, I ask for it, because I want them proud to post it. A week or so later, I book a short debrief to walk them through what we made and to hear how it landed.

None of that asks the guest for anything. It's a set of small gifts that make the guest look good in front of their own network. And because the guest shares it, people in their network see the conversation, and some of them become guests too.

There's a version of this that turns sour, and I've seen it. If you treat every guest as a lead and push a pitch the moment the stream ends, the guest feels it. Everything good about the conversation goes away. I'd rather leave the door open and let the relationship decide what comes next. It might be business, or an introduction to someone else, or a friendship. Any of those is enough.

What would you send a guest the day after a conversation to make them glad they came?

Turning the misses into something lasting

Sales is a numbers game, and most conversations don't end in a deal. I don't say that to discourage anyone. It's simply how markets work. If you talk to a hundred potential customers, a few of them buy and most of them don't.

What I love about the show is what it does with every conversation that doesn't end in a sale. In a normal sales process, a conversation that doesn't close disappears. You spent the time, nothing came of it, and nobody else ever benefits. On a show, every conversation becomes a piece of media that keeps working. Somebody watches it next month and learns something. A guest shares it and their followers find you. The conversation that didn't close still created something.

That changes how I feel walking into each one. I'm not carrying the weight of needing a particular outcome, because the conversation is worth having on its own terms. That lightness comes across, and people respond to it. I think it's the single biggest reason guests come back for a second episode.

How many of last month's conversations left behind anything you could share?

Building your own show

You don't need a studio or a famous name to start. You need a reason to talk to the people you want to know, and a place to put the conversation. Here's the sequence I'd follow if I were starting from nothing today.

Start with the list you made at the end of the introduction. Those are the buyers, investors and operators you most want to understand. Name a show after the conversation you want to have with them, something plain that says what you talk about.

Invite them as guests. Write to them about their work, what you admire about it and what you'd like to ask. Keep it short. Leave your company out of the invitation, because the invitation is about them.

Prepare properly. Read what they've written, watch their talks and come in with questions only someone who did the homework would ask. The quality of your questions is the gift, and guests notice it.

During the conversation, put the spotlight on them and keep it there. Ask about the hard parts. Let silences sit. Your job is to make the guest look as smart as they are.

After the taping, give generously. Send the links, the clips and the page. Book a short follow-up to see how it went. Then let the relationship grow at its own pace.

Do this every week for a year and you'll have spent a year in deep conversation with the people who matter most to your company. I can't think of a better position from which to find your first customers, and that's where the next chapter begins.

Which guest will you invite first, and what's the first question you'll ask them?

Chapter 04First Customers

Mike Ma invests at pre-seed and seed through Sidecut Ventures, and he's looked at thousands of pitches. When I asked him what kills companies at the earliest stage, he answered without hesitation. Products are easier to build than ever and capital is easy to find, and still, as he put it, "They die for a lack of customers."

That line frames this chapter. Your first customers do more than pay you. They tell you whether the problem is real, whether your answer fits it and whether anyone will tell a friend. Every guest who'd built something lasting could name their first few customers and say how each one arrived.

Sign before you build

Sameer Pirani has built payments technology and now works with early founders at Brinc. He told me the one move he'd make again on any new venture: "before I spent the time on engineering or the solution on any technology side, I had 3 MOUs signed with clients that were gonna use the technology."

Three signed memoranda, before a line of code. Sameer wanted proof that someone would use the thing before he spent a year building it. The trap he warned about is the one most technical founders fall into, the belief that a great product will find its own buyers. He named it plainly as "thinking that if I build something great, people are just gonna come to it."

You can argue about whether an MOU is a strong enough signal, and Sameer would agree it's an early one. My point is simpler. He went to the buyers first and asked them to commit to something on paper, which forced a real conversation about what they needed.

Who are three customers who'd sign something today, even a letter of intent, if you showed them what you plan to build?

Your reputation is your first channel

Robin Park co-founded Chaparral Labs, which helps scientists find drug targets faster. Before the company existed, he'd spent years in proteomics and bioinformatics, and people in his field knew his work. When he started selling, he didn't have to introduce himself. His first customers came because they "already knew my work and trusted our technical expertise."

Robin's team spent more than two years building a data platform before adding any AI to it. They had paying customers from industry and academia during that time, and he told me the traction came without a formal sales or marketing program. The relationships he'd built as a researcher did the work a sales team would have done.

Natalie Kaminski's first customer arrived the same way. She was freelancing as a product designer and took a gig with a small investment firm in New York. She described the end of it this way: "by the end of that gig, I've designed a platform that they really liked and they said, could you build it for us?" That request became the first project for JetRockets, the software development company she co-founded.

Marlon Tesla, an engineer who spent years in subsea controls before founding Tesla Solutions, told me a slower version of the same story. He did consulting for a few years to keep the company alive, and it was through those consulting relationships that he found operators willing to take a risk on a new vendor. In his words, they said yes "because we'd built trust with them." That trust took years of small commitments delivered on time.

What have you already done for someone that you could turn into your first sale?

Narrow until it hurts

Christian Brown co-founded Glewee, an influencer marketing marketplace. He was honest about how long it took them to find their footing: "For a while, we wanted to be the everything company for the everything brand for everyone." It didn't work. In his words, "When we first found really good success, it was when we started niching down."

Ajay Bam learned the same lesson at an earlier company and brought it into Vyral, which makes video searchable and shoppable. He told me "you can't as a small startup, you can't serve every single vertical in your market at the beginning." Choosing one segment felt like leaving money on the table, and it was the only way his team could serve anyone well.

Chetan Saundankar built Coditation, which helps enterprises turn AI into business outcomes, by starting smaller than his ambition. He said "initially we started with mid-market before moving to enterprise." The mid-market work gave his team case studies, and those case studies were the proof larger buyers asked for.

I'll admit narrowing is hard for me. I like talking to everyone, and the show reflects that. But when I look at the companies on my list that broke through, almost all of them could describe their first customer in one sentence, down to the role and the size of the company.

Can you describe your first ten customers in a single sentence, and would they recognize themselves in it?

Do the unglamorous work by hand

Christian's early days at Glewee were anything but elegant. Before the platform worked at scale, he told me they were "begging our friends to take the $50 deal for the Instagram story just to prove it worked." They needed a few small transactions to show brands and creators that the marketplace was real, so they made those transactions happen one at a time.

I hear stories like this from almost every founder who's made it through the early years. The first deals were done manually, sometimes awkwardly, often for less money than the founder wanted. What mattered was that each one taught them something they couldn't have learned from a survey.

Pianpian Guthrie, who founded Amotions to build AI that reads emotion in sales conversations, started with a broad mission and narrowed it once she started selling. As she put it, "As I started doing founder-led sales, like, wow, sales is really challenging." That experience pushed her team to focus on sales conversations, because she'd felt the pain firsthand. Her first traction then came from a place she hadn't targeted at all, a hearing clinic that found the company on its own.

Doing the early sales yourself teaches you what your customers need in a way no hire can. You hear the objections in their words and see where the product confuses people. Over time you learn which promises land and which ones make people's eyes glaze over.

Which part of your first sale could you do by hand this week, before you automate any of it?

Let a real problem call you back

Shivoh Chirayil Nandakumar finished a PhD in robotics and founded RideScan AI, which monitors deployed robots for safety and reliability. He told me about his first paying customer. He'd shown a demo to the CTO of an integrator who sells robots to enterprises, and nothing happened. Then, in his words, "after two months, the CTO called me back."

A robot the integrator had deployed had made an error that their existing software couldn't see. Shivoh's system could. The integrator came back with a real problem in hand, and Shivoh said "they paid upfront."

I love this story because it shows what a good demo does. It doesn't always close on the day. It plants a solution in someone's mind, and when the problem shows up in their world, they remember who had the answer. The demo did its work two months later.

The lesson I take from Shivoh is to show your work to the right people early and often, then stay in touch without pushing. When the pain arrives, you want to be the first name they think of.

Who have you demoed to in the last six months that you haven't followed up with?

Listen to what customers do

Karin Stephan leads growth at Sidekick, which turns an expert's body of work into a conversational channel. She described growth as a daily experiment on your understanding of people: "you put your understanding of people to the test every day." You find out whether they care enough to try the product and whether they come back.

I think that's the right attitude toward first customers. Each one is a test of a hypothesis you hold about people, and the results are often humbling. The customer who you were sure would love it never logs in, and the one you almost didn't call becomes your best reference.

Mike Ma doesn't invest until he's watched a founder work through this process. His firm coaches founders for thirty days before writing a check, and he explained why: "It's hard to fake your way through 30 days of watching go-to-market." He told me about one founder who discovered during those thirty days that their best customers were government buyers, a market neither of them had expected.

That discovery came from doing the work in front of someone who was paying attention. You can get the same benefit by keeping an honest log of every customer conversation, including what you expected and what happened.

What did your last five customers do that surprised you, and what does it say about who your product is for?

The first ten

If I had to compress this chapter into a practice, it would be a list. Write down the names of the first ten customers you want. Beside each one, write how you'll reach them, and make it a way that gives before it asks. The show from the last chapter works, and so does a piece of work you do for free or an introduction from someone they trust.

Then go get the first one by hand. Learn from it, adjust, and go get the second. Robin, Natalie and Marlon all reached their first customers through work they'd already done for people. Christian and Pianpian got there by selling it themselves until they understood the problem. Shivoh got there by showing his demo and staying patient.

None of them had a growth engine yet. That comes next, once you know who your customers are and why they buy. Who's the first name on your list of ten?

Chapter 05Distribution That Compounds

Once you have a handful of customers who love what you do, the question changes. You're no longer asking whether anyone wants this. You're asking how more of the right people find out about it without you personally carrying every introduction.

The guests who answered that question best had something in common. Their distribution got cheaper and stronger over time, because each piece of it built on the last. A post that made someone feel something led to a relationship, which led to a deal, which led to a story worth telling. This chapter is about building that kind of loop, starting with the approach from chapter two and widening it.

Tell the story only you can tell

Jarrett Thomas founded More Than Media to help founders tell their stories and build relationships on LinkedIn. He learned it by doing it. He was working in sales, posting on LinkedIn to a small following, and getting nowhere on the bad days. Then he wrote about how he'd gotten into sales in the first place, with photos and the honest details, and he told me "That one post got 100,000 views and over 200 DMs."

He kept going. Around the same time he was recognized as a LinkedIn voice to follow, and then the payoff arrived. In his words, "on day 89, I ended up closing a deal for $450,000 a week before the pandemic." The deal came from a close connection who'd been watching his posts.

Jarrett's rule for what to post is the simplest one I've heard: "Anything that you post should make somebody feel something, even if it's about business." A polished summary of your wins won't do that. The honest story about the bad day does, because the reader recognizes themselves in it.

I'll add one thing from my own experience. The show gives you an endless supply of stories that aren't about you. Every guest says something worth sharing, and posting their best line puts the spotlight on them while it reaches your audience. That's giving and distribution in the same move.

What's the true story about your company that you've been too polished to tell?

Let your work become your content

Joe Toscano was featured in Netflix's The Social Dilemma and wrote a book called Automating Humanity. Now he runs Service Stories, which turns the work orders of service businesses into content that search engines and AI assistants can find. His insight is that the best content already exists inside the business.

He put it this way: "We don't have to guess what your customers are going to chat with the internet about because they literally chatted to your people at the front" desk. Every repair, every question at the counter, every job completed is a record of what customers care about. Turn those records into pages, and the business becomes the obvious expert to anyone searching for that problem.

His example has stayed with me: picture two auto shops side by side. One has a generic page about air conditioning. The other has a dedicated AC service page and twenty articles about real repairs across different years, makes and models. Which one would you call?

Joe also said something about selling that belongs in the next chapter, and I'll repeat it here because it shapes how he thinks about content: "I actually don't try to sell AI. I try to sell outcomes." The content works when it brings in calls and form fills. Rankings are a means to that.

Which records of your daily work could become pages that answer your customers' questions?

Get found by the answer engines

Mariya Pallais runs Pinkfins, which helps local businesses get found by AI assistants. She pivoted her firm from public relations into what's now called answer engine optimization, making sure ChatGPT, Claude, Gemini and Perplexity have enough accurate information to recommend you.

Her first test was her own company. She added structured markup to her site so an AI could read "what exactly this is and who exactly this is for," in her words. The leads that came through her website contact form started closing at a rate that surprised her. When I asked about it, she said "our close rate is like 80%, 90%." That's what happens when the people arriving already understand what you do before they reach out.

Pianpian Guthrie, whom you met in the last chapter, saw the same effect from the other direction. Her first traction came from a hearing clinic that found her company by asking Google's AI for a solution. She'd never targeted that industry. The answer engine made the match on her behalf.

This is a new channel, and it rewards the same thing the show does. Specific, honest material from your own work gets cited. Generic explainers get ignored, because the models already know them.

If someone asked an AI assistant for a company like yours today, what would it say?

Package your insight as news

Itay Kahana built Watchful to track what competing apps ship. In the early days he had something nobody else had, which was data about what large companies were changing in their products. He turned that into a distribution machine. As he described it, his team got into the habit of "taking these insights" and packaging them into stories for TechCrunch, Business Insider and other outlets.

The coverage was free, and it brought in inbound interest from the exact companies he wanted as customers. They read about a competitor's move and wanted to know what else Watchful could see.

I think every company has some version of this. You know something about your market that the market doesn't know about itself. Maybe it's a pattern across your customers, a number from your data or a trend you see before anyone else. Shared generously, that insight makes you the source journalists call.

Itay also told me about a mistake he made with distribution, and it's worth hearing. In the early days he ran Watchful's sales and marketing from Israel, and in his words "It was very difficult and it was a mistake when I'm thinking about it." Being close to your buyers matters, even in a world of video calls.

What do you know about your market that would make a good headline?

Borrow trust from partners

David Gompert runs Avant-Garde Trading, a retail brokerage built around service. He doesn't buy television ads. Instead, he explained, "we have relationships with a lot of publishers of these newsletters." Those publishers already have the trust of the readers David wants, and the relationship brings customers without a big ad budget.

James Vanreusel built Vanreusel Ventures, a finance and accounting platform for startups, on a similar foundation. He gets referrals from large accounting firms that can't serve certain clients because they're doing those clients' audits, from corporate attorneys running fundraisings and from bankers building models. Every one of those partners sees his ideal customer before he does.

Aleksandar Hadzhiyski, who runs Titan Agency for consumer brands that sell online, told me most of his recent clients came from referrals. He was candid that this felt unreliable, and he's building a personal brand and agency partnerships so growth doesn't depend on whoever happens to mention him that month. I respect that he named the weakness while things were going well.

Who already has the trust of your customers, and what could you give them that would make an introduction natural?

Solve one problem for one customer, then sell it to their peers

Stuart Frost has founded several companies, taken one public and sold another to Microsoft. Today he runs Geminos, which builds causal AI for enterprises. He gave me the cleanest example of compounding distribution I heard all season.

Great Western Railway in the United Kingdom had a problem with delay attribution. When a train runs late, the company has to work out why and compensate passengers, and the process was slow. Stuart's team built a system, and it was accurate enough out of the box that the customer signed. He told me "I think 8 weeks later, we delivered the full system."

Then came the part that compounds. In Stuart's words, "every train company in the UK has that same problem. So we're now selling to all of them." One thorough solution for one customer became a product for an entire industry, and the first customer became the reference that sold the rest.

Parag Vaish has led product at Microsoft, Tesla and Google, and he now builds custom AI at NextNow. He told me most of the hard problems he sees in his customers' companies are distribution problems, not engineering ones: "All of that's go-to-market related problems." He shared a story about a customer that sells to school districts. His team worked from first principles to find where districts discuss their needs in public, and they ended up on YouTube, where school boards post their meetings. They found that 8,000 of roughly 13,000 districts had video there. That became a map of every buyer's stated needs.

Which customer problem have you solved once that every one of their peers also has?

Patience is part of the channel

Jay Frank is building a cooking show around cannabis in New York. He told me about reaching out to a leader in the cannabis community on LinkedIn. The conversation went well and led nowhere. Then, a few months later, an email arrived from that person asking where the show stood and saying he wanted to be on it.

Jay treated that email as validation, and he was right to. Distribution built on relationships rarely pays off on your schedule. You plant a seed with a good conversation, and it grows when the other person is ready.

This is where the show earns its keep for me. Every guest I've hosted carries a small memory of a good experience with my name on it. Some of them call months later with an introduction or an idea. A few become customers or partners. I can't predict which, and I've stopped trying.

What would change if you judged this quarter's outreach by the relationships it started rather than the deals it closed?

Building your loop

Here's how I'd put the pieces together. Start with the show, because it gives you a steady stream of conversations with the people you most want to know. Post the best moments from each one, with the spotlight on your guest. Turn what you learn into pages that answer what your customers ask, the way Joe does. Then make sure the answer engines can read them, the way Mariya did.

When you notice something about your market that nobody's written down, package it as news, the way Itay did. Find the partners who already have your customers' trust and give them a reason to introduce you. And when you solve a problem well for one customer, look for every peer who has the same problem, the way Stuart did.

Each piece feeds the others. A guest becomes a post, the post becomes a relationship, the relationship becomes a customer and the customer becomes a story. Over a year, that loop does more than any single campaign could.

Then you'll face the moment this whole loop exists to create, which is the conversation where someone decides whether to buy. That moment deserves a chapter of its own. Which piece of the loop will you build first?

Part 04The close

Chapter 06How to Close

Everything in the last three chapters leads to one conversation. Someone who has your problem is sitting across from you, and they're deciding whether to commit. You've given generously to get here. Now you have to help them say yes.

I gave closing its own chapter because so many good founders stall right here. They can start a conversation with anyone and they can't finish one. The guests who'd closed large deals talked about closing with surprising consistency, and very little of what they said was about technique. It was about preparation, value and a willingness to say the number.

Lead with something they don't know

Itay Kahana landed his first enterprise customer for Watchful before he had a finished product. The story started when a large company tried to hire him. He told them he was starting a company, they asked what it did, and the business owners wanted to hear more. Itay ended up in a room pitching, by himself, with no product to show.

What he brought instead was insight. As he put it, "First of all, I led with data. So I didn't just give them a pitch and like did a very generic pitch. I gave them data about the competition and stuff that they didn't know."

That's the move I'd copy. A buyer has heard every pitch about why your company is great. They haven't heard the thing you learned about their market last week. When you open with something useful to them, the meeting stops being a pitch and becomes a working session, and people buy from the person who taught them something.

Itay was honest about what happened next, and I appreciated it. When they asked his price, he invented one on the spot, and they said yes immediately. His reflection: "So maybe it was a too low number." He also said his early product bent too far toward that first customer's feature requests before he'd researched the wider market. Both lessons are worth carrying into your first big deal.

What could you teach your next buyer about their own market before you ask them for anything?

Translate everything into money

Anders Teigland is a battery materials founder, a scientist by training who's spent his career turning research into products. He described the shift every technical founder goes through in front of buyers. You start out talking about the science, and eventually you realize that "the only argument you can make is money, either on the bottom line or on the top line."

His customers didn't buy a better anode because it was elegant chemistry. They bought it because it charged faster or cost less, and that showed up in their numbers. Anders learned to lead with the number and let the science support it.

Joe Toscano said the same thing about AI in the last chapter, that he doesn't sell the technology: "I try to sell outcomes." The technology is how you deliver. The outcome is what the buyer signs for.

I find it useful to write the outcome as a single sentence before every important meeting. It names what the customer will have, in their terms and with a number, after they buy. If I can't write it, I'm not ready for the meeting.

What's the one sentence, with a number in it, that says what your customer gets?

Don't be the cheapest

Pricing came up again and again on the show, and the advice was consistent. Christopher Nelson, who founded Alpha Hire, put it plainly: "you never want to be in a position where you're always the cheapest guy." Competing on price creates a whole set of problems, from thin margins to customers who'll leave the moment someone undercuts you.

Yariv Adan helped start Google Assistant and Google Lens, and he now invests through Ellipsis Venture. He sees the price pressure getting worse as AI makes capabilities cheap to copy. His warning was sharp: "if you are not differentiated, you fight on price every single transaction."

The answer to both is differentiation that a buyer can see in the meeting. Itay's competitive data was differentiation. Anders's faster-charging anode was differentiation. When a buyer can see what only you can do, the price conversation gets much easier, because they're comparing you to the cost of the problem instead of to a cheaper vendor.

Say the number plainly when you get there. I've learned to state my price in one sentence and then stop talking. The silence after a price is uncomfortable, and the founder who fills it with a discount usually regrets it.

When a buyer compares you to an alternative, what do they see that the alternative can't offer?

Sell confidence, not fear

Marlon Tesla builds monitoring technology for equipment on the sea floor, where a failure is expensive and hard to reach. He was clear about where his company draws the line: "We choose not to sell fear to sell our products and services." Instead, they focus on how fast they can detect a problem and the confidence that gives the operator.

I think that's right, and it fits the giving approach. Fear works for one sale. Confidence builds a relationship where the customer comes back, because working with you made them feel more capable instead of more anxious.

Parag Vaish told me a related story from his time at Evolv, which builds weapons detection for public venues. When the stakes are life and death, he said, you thread the needle by giving the buyer the power, and with it the responsibility, of making the decisions. His team let buyers choose the detection sensitivity themselves. The buyer owned the tradeoff, and that ownership built trust in the system.

How could you leave your buyer feeling more in control after the meeting than before it?

Make it obvious

Maurice Harary runs The Bid Lab and built software that helps small businesses find and win government contracts. Writing proposals that win is his whole job, and his first rule is simple: "Make it obvious for the person reading it." The evaluator might know nothing about what you do. Your job is to make the decision easy for them.

He also told me about the bid he lost that taught him the most. It felt like it had been written for his company. But client work came first, so he waited until the last second and pulled it together in a rush, doing everything he tells his own clients not to do. They lost, and the agency even called to ask what had happened. When the contract came up for renewal the following year, he took it seriously, and they won it.

Maurice talks about the psychology of winning, and he said "there's also a psychology to losing." A loss you were sure you'd win stings in a specific way, and he used that sting to prepare harder than he ever had. The contract is now one his team doesn't take for granted.

Stuart Frost's railway deal from the last chapter closed for a related reason. His team's system was so accurate out of the box, after only a few days of work, that the customer was "just blown away" and signed. The proof made the decision obvious.

Is your proposal written so that someone who knows nothing about your field could say yes to it in five minutes?

Close the relationship, not just the deal

Jarrett Thomas, whom you met in the last chapter, closes deals by building relationships first. He told me that "usually when you build a relationship, the problem that they need to solve will always show itself." When you've listened long enough, you don't have to guess what to sell. The customer tells you.

Harvey Berman, who has led sales teams for years, taught his people to treat every customer conversation as a way to earn the next conversation, not to force a close. He said he was never trying to get every last dollar or win a quick transaction. He wanted to help the customer with what they were trying to do, and that patience is what brought them back.

That matches my own experience. On the show, I never pitch on air. The guest came to talk about their work, and that's what we do. If there's room to work together, it shows up later, in the debrief or a follow-up call, and it shows up because the guest raised it. I don't have to push, because the relationship already did the work.

Running a lot of conversations helps here in a way people don't expect. When my week is full of good conversations, no single one has to close. I don't walk in worried about my rent or my quarter, and I think buyers can sense that. What they see is someone focused on how to help, and that's who people want to buy from.

How many good conversations would you need on your calendar so that no single one feels like it has to close?

You're better at this than you think

Sam Kamani has interviewed hundreds of founders on his podcast, and he told me the second biggest thing he's learned about the good ones. They're very good at sales, and "most of the times they don't even know that they are really good at sales."

I hear a lot of founders say they're not salespeople. They picture someone pushy with a script, and they don't want to be that person. But the founders Sam described sell all the time. They sell investors on the vision, recruits on the mission and customers on the outcome. They do it by caring about the problem and explaining it clearly.

If that's you, you don't need to become a different person to close. You need to prepare, lead with insight, say the number plainly and then listen. Everything else in this chapter is detail on those four habits.

Before your next important meeting, write down the insight you'll open with, the outcome sentence and your price. Which of the three is hardest for you to write?

Part 05Capital and people

Chapter 07Fundraising

I've spent a lot of time on both sides of the fundraising table, and the show put me in conversation with dozens more people who live there. Some run funds. Some raised from angels, families or their own communities. A few decided they didn't want outside money at all, and they were glad they made that call.

I was surprised by how much of the advice repeated what you've already read in this book. Investors are buyers, and the round is a close. The guests who raised well had built relationships long before they needed a check, led with evidence instead of a pitch and chose their investors as carefully as their investors chose them.

Start the conversation before you need the money

Vaishali James founded Sangatna Angels, an angel network that funds women founders. Before she launched it, she spent a year on research and talked with somewhere between two and three hundred founders, investors and mentors. By the time the network went live, the people she'd spoken with were ready to send founders and to invest.

She coaches founders to do the same thing with their own raises. As she put it, "We tell them that they have to hit the whole investment or the funding conversation way before they even realize they need the money." When the need arrives, you want to be calling people who already know your story, not introducing yourself.

She learned this the hard way at an earlier fintech company. Investors kept asking to see a larger loan book before they'd invest, and she needed the investment to build that loan book. Starting earlier, with people who could watch the business grow, is how she'd break that loop today.

Aviv Frankel's story from chapter two belongs here too. Some of his investors came from conversations on his podcast, long before he asked any of them for money. That's what starting early looks like.

Who are the ten investors you'd most like on your cap table, and how could you start a relationship with each of them this quarter?

Treat every no as data

Vaishali gave me the healthiest framing of rejection I heard all season. When an investor passes, she said, "It's not a rejection, just collect it as data." The reasons investors say no, and the preparation you did for the meeting, are useful information about your business and your pitch.

I like this because it turns the raise into a learning process. If five investors pass for the same reason, that reason is probably real, and you can fix it. If they pass for five different reasons, maybe you're talking to the wrong investors. Either way, each meeting teaches you something.

Mike Ma described the investor side of the same idea. Before he raised a fund, he wrote more than twenty angel checks, and he admitted he made some of them on pedigree or other people's opinions. Several didn't work out, and he kept asking what he'd missed. The answer changed how he invests.

What did your last three investor conversations teach you, and what will you change before the next one?

They're buying the founder

Mike's conclusion from those early checks shaped Sidecut Ventures. After looking at thousands of pitches, the one thing he's certain of is that the founder is the asset. In his words: "what asset are you writing? You're writing the founder."

That's why he now coaches founders for thirty days before investing. He watches how they work through go-to-market in real time, because that tells him more than a deck. And he's candid about why the relationship matters so much: "the average time I'm on your cap table is a decade." He framed the thirty days as something like dating before the commitment.

Ed Lafferty, co-founder and CFO of Saturn Partners, an early-stage venture firm, said the same thing from a different angle. His partner taught him to assess a management team beyond the numbers, because you're investing in people, not just a product. He values founders who come to him when something goes wrong: "he tells you that he screwed up and here's what he's going to do to fix it. You know, that transparency is super important."

If an investor watched you work for thirty days, what would they learn about you that your deck doesn't show?

Show adoption, then ask for fuel

Sameer Pirani, whom you met in chapter three, gave founders advice that sounds backwards at first: "you shouldn't be focused on raising capital per se, but more on the adoption side." If customers are adopting your product, staying longer and telling others, those are the signals any investor wants to see.

Michel Friedman invests in supply chain, logistics and fintech in emerging markets through Reflect Ventures. He was blunt about his own bar: "We're not investing in ideas. You got to have revenue and some kind of traction. You better know the industry you are in." For many investors the raise starts with proof. That proof comes from the work in chapters three through five.

Madhukar Bhatia, whose story opened chapter one, asks every founder whether they understand their market and have a unique insight into it. The best answer to that question is a set of customers who already pay.

What's the strongest piece of evidence of adoption you could put in front of an investor this week?

Choose your investors carefully

Several guests reminded me that the choosing runs both ways.

Michel had a warning I've repeated to a lot of founders since: "if an investor tells you that he's very confident that he can always pick winners, you don't want his money." Early-stage investing involves a lot of misses, and an investor who won't admit that probably won't handle your hard months well.

Bernard Harguindeguy sold GreenBorder to Google and later sold Elastic Beam to Ping Identity. These days he invests in cybersecurity, and he told me what he wanted from investors when things got hard as a CEO: you don't want to be alone, and "you don't want investors criticizing you at that moment instead of supporting you."

Karl Clark spent thirty years in automotive engineering at Ford before building AI tools for the industry. He wants investors with deep connections in his space, because when those investors put money in, "they can make a phone call." An investor with the right network can open doors you'd spend a year knocking on.

Jim Donnelly, the six-time founder building longevity clinics, has the simplest filter of all. He told me "I'm going to raise money From people that I like, life is short." He's at a point in his career where the work has to be enjoyable, and the people on his cap table are part of that.

Which of your current or potential investors would you call first on your worst day, and why?

Fit the money to the business

Not every company fits the venture model, and several guests made a strong case for knowing which kind you're building.

Yaniv Feldman built Flag Capital around the gap. He pointed out that if you build a company that reaches five or ten million dollars a year in recurring revenue, "a VC can't do anything with you" because you're not on track to the size their fund needs. His firm targets those companies, with smaller exits, secondaries and dividends as the paths to a return.

Ken Deering, who founded iGuard to prevent kitchen fires for people aging at home, ran into the model's limits from the other direction. Choosing to build hardware, he said, "wiped out 90% of the available investors immediately," because so many funds are built around software and biotech.

Gregg Bauer, managing partner at ScaleUp Labs, explained how the expectations change across regions. He said that in Latin America and Europe "capital is generally applied as a cash flow exercise," with investors looking for profit and dividends, while American investors fund for valuation growth. That mismatch can stall a company trying to expand into the United States with a European cap table. He added that some investors on the West Coast "won't touch a founder unless that founder has failed at least once," which tells you how differently each culture treats failure.

Gregg's own program is selective. He told me ScaleUp Labs takes one cohort of ten companies a year from roughly six hundred that apply. If you're applying anywhere that selective, the approach in this book gives you a better chance than a cold application.

Rachael Richardson, an investor at Florida Funders with a background in climate and impact funds, described the two ways she sees investors win over the long term: "One's gonna be like relationship and access to capital and one's gonna be like hyper expertise." Knowing which kind of investor you're talking to helps you pitch them well.

Which kind of capital fits the company you're building, and are you talking to investors who provide it?

Sometimes the best investor is your customer

Some guests made the case for raising less, or later, or from somewhere unusual.

Marlon Tesla self-funded his subsea monitoring company and took consulting work to keep it alive. Looking back, he said "staying separate from outside investor money allowed us to stay afloat long enough to find paying customers." He acknowledged that outside money might have sped up development. It also might have pushed him to run out of time before customers arrived.

Luca Pandolfi took a different path with Woodland Bio. His company needs to build a large facility in a rural community, which is the kind of project that can draw local opposition. He put a controller on the team who grew up in that community, and he told me "He's that person that people trust." Luca said almost all of the company's investment so far has come from that community. The people most affected by the project became its backers.

James Vanreusel, who runs finance for startups, gave me a reminder that applies whichever path you choose: "expenses are certain, revenues are uncertain." He advises founders to keep a budget the board approved and a separate real-time model that gets updated every week or month, because the gap between plan and reality grows fast. Investors will eventually want to see the numbers and the unit economics, and it's far better to have them ready.

What's the least money you'd need to reach your next real milestone, and who besides a venture fund might provide it?

Raising the way you'd sell

When I step back from these conversations, the raise looks a lot like the sale. Build relationships long before you need them, then lead with evidence and an insight the investor doesn't have. Say the number plainly. And you choose people you'd want to work with for a decade, because you probably will.

The show helps with all of it. Many of my guests are investors, and the conversation on air gives both of us a way to get to know each other with nothing on the table. When the time comes to raise, those conversations are already underway.

The next chapter is about the people you'll hire once the money lands. Before you go there, write down the five investors you'd most want to talk to, and what you'd want to learn from each of them. Who's at the top of that list?

Chapter 08Team and Leadership

At some point the company outgrows you. Your customers and your capital now depend on people other than you, and the quality of those people decides what happens next. My guests had plenty to say about hiring, and even more about the harder job of leading people once they're in the room.

Nobody is ready for the job

Joel Trammell has been a CEO for most of his career, sold companies to CA and NetApp, and now teaches CEOs through Xpertloop. His opening claim made me laugh with relief: that the unique things about the CEO role make it "impossible to really be qualified or ready to go when you first get it."

He learned an early version of this at the Naval Nuclear Power School, surrounded by brilliant engineers. In his words, "just because we had a bunch of smart people, it didn't mean the organization ran well." Running an organization turned out to be a separate skill, and a generalist one, unlike anything a specialist career prepares you for.

What bothers Joel most is watching a CEO waste a good position because they won't ask for help. He described it as seeing someone turn what should be a home run into a single or a strikeout. The fix is humbling and simple. Find people who've done the job and ask them.

Sameer Pirani said the same thing about his own early years: "I would definitely surround myself with more people that have been in the position that I want to be in at a much earlier stage."

Who has done the job you're doing now, and when did you last ask them for advice?

Culture is the part nobody can copy

Dave Clare founded Circle Leadership and has spent more than twenty years in leadership work. He told me about the moment his thinking changed. The leaders he coached would learn new behaviours and then go back to organizations whose culture made those behaviours impossible. Culture was the constraint, and it ate the training.

His conclusion became the core of his work: "the only thing that can't be copied is your ability to capture the spirit of your people." Competitors can copy your product and your pricing. They can't copy the way your people feel about working together.

He also reframed the human resources function in a single line that I wrote down on the spot: "we should have resources for humans, not humans as a resource." It's a small shift in words and a big one in how you treat people on a hard day.

Natalie Kaminski arrived at the same place through a painful stretch at JetRockets. The company grew fast while margins shrank, and people were burning out. She had to face the question squarely about whether the money was worth it. Her answer reshaped the company around a single question: "what kind of company do we want to work for?" She chose a smaller company with radical honesty over a bigger one nobody enjoyed.

If your team answered Natalie's question today, would they describe the company you're running?

Make it safe to disagree

Ajay Bam built and sold a company before founding Vyral, and he told me what he does differently the second time. Beyond focusing on one vertical, he builds a culture where people speak up. He described it as "empowering your team to talk to your customers without asking your permission," and, most of all, "you're empowering your team to criticize both your leadership and anyone in the company with respect."

That last part takes courage from a founder. It means hearing that your plan is wrong from someone who reports to you. It also means you find out sooner, while there's still time to change course.

Gordian builds tools that help people structure decisions, and he talked about the person in every meeting who has the answer and stays silent. His view is that good systems give that person a voice while keeping the decision with them. In his words, "So the decision ownership stays with the employee, and this is the core." He pointed to a Siemens example where machine operators got recommendations from AI and kept the final call on their own machines.

Ed Lafferty, whom you met in the last chapter, values that kind of honesty from founders, and I think it starts with leaders who reward it. When someone tells you they made a mistake and how they'll fix it, the way you react decides whether anyone ever tells you again.

What happened the last time someone on your team told you that you were wrong?

The first hire sets the culture

Scott Finkelstein coaches founders and is building an AI coaching app at Yutavis. He was emphatic about early hiring: "that first hire is so important to maintain and grow your culture or potentially implode it."

He told me about a client who hired a polished salesperson against his advice, because the candidate looked great on paper. Scott felt the fit was wrong for a small company's culture. Within six months the person was gone, and the company had a lot of issues to clean up afterward.

His point is that skill alone won't save a hire who doesn't fit. In a small team, every person shapes how the others work. A bad early hire costs more than their salary. It costs the habits they teach everyone else.

If your next hire copied the habits of your current team, would you be happy with the result?

Look where the talent is

Some of the best hiring stories on the show came from unexpected places. Benton Calder, who helped build commerce systems at Shopify before starting a private home AI company, needed a hardware engineer. He searched LinkedIn and the usual sites, then found that "the best place with the most amount of people was Reddit." The engineer he hired holds a master's in nuclear engineering and builds hardware that flies on satellites.

Addison Houston met his co-founder at Arbit Financial the same way. He'd posted about his idea for making solar more affordable, and a talented engineer in Chicago read it, filled out the form on his site and reached out. As Addison put it, "He found me. I made a post or 2 on Reddit."

Both stories are another version of the giving approach. Benton and Addison put their ideas out in public where the right people could find them, and the right people came.

Aleksandra Łoś, who co-founded Relayn, added a caution about co-founders that I hadn't heard before. She stressed how much it helps to have a co-founder close by, ideally someone you can meet daily and who speaks your native language. She also recommended agreeing on how you'll communicate from the very beginning, what she called "So-called the communication contracts." Hard conversations go better when you've agreed on the rules before you need them.

Where are the people you want to hire talking about their work in public, and have you shown up there?

Lead the humans and the machines

AI changed many of my conversations about teams this year. Aleksandar Hadzhiyski, who runs Titan Agency, was asked by the market to cut staff and replace them with AI. He went the other way. He decided "instead of replacing my team, I should empower them and provide them with the AI tools they need to deliver." His team of specialists now does more with the same people.

Dave Clare argued that everyone in a company will soon need to understand leadership, because many people will be directing several AI agents as part of their job. You don't need to become a manager to need the skills of one. Gordian's point about decision ownership fits here too. The person closest to the work should keep the final call, even when a machine makes the recommendation.

I think this is one of the biggest leadership questions of the next decade, and I don't claim to have the answer. What I've seen work on the show is the same principle that runs through this book. Treat people as the point of the company, give them the best tools you can find and ask them what they need.

What would your team do with an extra two hours a day if the right tools gave it back to them?

Leadership is lonely, so don't do it alone

Scott Finkelstein told me about a dinner where it hit him that he was alone with his company. Nobody around him understood the weight of it. In his words, "I decided in that moment of realizing I was alone to reach out to one of my mentors and reconnect with them." He found other founders in Austin, and he described that reconnection as a relief.

I relate to that more than I'd like. Running a company can isolate you even when you're surrounded by people, because nobody else carries the same set of worries. The show has been part of my own answer. Every week I get to sit with people who've carried the same weight, and every conversation reminds me I'm not the first to face whatever I'm facing.

Joel's advice and Scott's story point to the same habit. Build a small group of people who've been where you are, and talk to them before you need to. Then do the same for someone a few steps behind you.

Who are the three people you'd call tonight if your company hit a wall, and when did you last talk to each of them?

Part 06The long game

Chapter 09Scale and Exit

The last stage of the playbook is the one most founders picture first and plan for last. You've found customers, built distribution, closed deals, raised money and hired a team. Now the company has to work at a size where you can't touch everything, and at some point you may want to sell it.

The guests who'd done this had a lot of scar tissue, and they shared it generously. Their advice was less about strategy and more about building a company that doesn't depend on any single person, customer or demo.

Demos lie at scale

Shivoh Chirayil Nandakumar, whose RideScan AI story opened chapter three, sees a gap in robotics every day. Robot demos look flawless because they're tuned for the demo. As he put it, "optimized for the demo but not for the real scale." His company exists because the problems appear once robots leave the lab.

Stuart Frost sees the same gap in enterprise AI. He told me the approaches large companies use have something like "an 87% failure rate to get from a demo to an actual production application." Getting from a working prototype to a reliable product is where most of the value, and most of the pain, sits.

Anders Teigland described the hardware version of it: "To go from piloting into large-scale manufacturing is a whole different beast." Benton Calder put it in a way anyone can remember: "building one of one thing is easy." Making thousands of them is the hard part.

What part of your product works today only because you're personally there to make it work?

Build a company that runs without you

Andy Harris advises founders on selling their companies at STS Capital Partners. He gave me a test I now use on every business I'm involved in. Imagine "if you left the business for the next 6 months, you took a hiatus." Would it keep running? If it wouldn't, you haven't built a company a buyer wants to own.

He named the two biggest detractors from value he sees in exits. One is founder dependence, which his test catches. The other is customer concentration, where one or a few customers make up half the business or more. Both make a buyer nervous, because the value could walk out the door.

Andy's most practical advice was to prepare long before you sell. He recommends founders "do a sell-side quality of earnings ahead of time," which is financial due diligence you commission on yourself before a buyer does it to you. You find the problems while you still have time to fix them.

If you took six months off starting tomorrow, what would break first?

Partners become buyers

Bernard Harguindeguy sold two companies, GreenBorder to Google and Elastic Beam to Ping Identity. He told me the pattern behind both: "Every one of the partnerships that you work with ultimately become a potential acquirer." By the time they're ready to buy, a partner already knows your company and where it would fit.

That's the giving approach again, playing out over years. Every partner you serve well is a relationship that might become an offer. Bernard's other piece of advice was about what makes a company worth buying in the first place. It has to fit a critical need in a market that's growing.

Sebastian Serrano made a related bet at Ripio. Around 2021 he chose to become infrastructure for other financial companies instead of fighting for retail customers. He reasoned that crypto would end up inside every financial app, and he wanted to be the layer underneath. Today, he told me, "almost every stockbroker that offers crypto in Argentina does it with us."

Which of your partners would be the most natural buyer for your company, and what are you doing to make that relationship stronger?

Deals are a slog

Joel Trammell, who sold companies to CA and NetApp, didn't romanticize either sale. His summary of getting a deal done was blunt: "It's a 6-month slog, and they're going to be all kind of twists and turns." In one sale, the company was running out of money and the deal ran late, and his team ended up borrowing money from the buyer to make the final payroll.

I share that story because the exit fantasy skips this part. The months before a sale are some of the most stressful in a company's life. You're still running the business while answering a buyer's questions, and anything can go sideways.

Elisabeth Cabanas, who invests for a family office, added a reminder that keeps the excitement in check: "a return is not real until the money is back into your account." A high valuation on paper isn't an exit. The deal is done when the money moves.

How many months of runway would you need to survive a sale that takes twice as long as planned?

Slow cooking works

Not every company needs to scale fast, and some of the strongest businesses on the show grew slowly on purpose. Shikha Miglani grew Saarthee for eight years on word of mouth before adding a sales team. She's building a product business now, and she isn't rushing it. As she put it, "Sometimes when you slow cook, the food is so yummy."

She also explained why the product matters. Her services business grew in a straight line, with more people bringing more revenue. Products grow differently, and she sees that as the way to break the link between headcount and revenue.

Nils Welin started a private security company after 9/11 with no background in the industry. The first two years were lean. He grew it to about 1,000 employees across nine offices, and then built a second company, ProGuard, after a year of planning before opening the doors. He summed up his career in one line: "it's hard to beat a guy who never gives up."

What would you build differently if you knew you had twenty years instead of five?

The long game

The guests who'd lasted longest talked less about tactics and more about character. Harvey Berman, who left a comfortable sales role to test himself in an industry where nobody knew him, said "Motivation fades. Discipline I can count on." Jim Donnelly's line from chapter one belongs here too: "a lack of options provides clarity."

Anthony Vinci, who builds forecasting AI at Vico, told me something that surprised me from a founder. His models have beaten his own instincts so many times that "I don't trust my gut anymore." Scaling a company means building systems that see more than any single person can, including you.

Leon Wankum, who wrote Digital Real Estate and founded oneVest, thinks about the very long game in his industry. He believes that over the next twenty years, "If you're a real estate company, you will be a Bitcoin company." I'm biased, since I've held Bitcoin since 2011, and I think he's right. Whether or not you agree, it's the kind of long view that shapes better decisions today.

What would you need to believe about the next twenty years to build your company differently this year?

What scale really asks of you

Here's what I take from these conversations. Build the company so it runs without you, starting long before you think about selling. Watch your customer concentration, and treat partners as the future buyers they might become. Commission your own diligence before anyone else does, and keep enough runway to survive a slow deal. And if your business suits a slower path, take it without apology.

Above all, the people who scaled well kept doing what got them there. They kept giving to customers, partners and their own teams, and the relationships carried them through the hard parts. Which of those relationships are you investing in today?

Chapter 10Afterword: Your Turn in the Chair

I started this book in a chair in Toronto, and I'll finish it there. Every conversation in these pages began with an invitation and ended with something given. The guest gave me their experience. I gave them the spotlight and my full attention. Neither of us asked the other for anything, and we both walked away with more than we brought.

That's the whole playbook in one exchange. The idea chapter asked you to find a problem you could stay with for a decade. The giving chapter asked you to reach people by inviting them in. The chapters on customers, distribution, closing, fundraising, team and scale all came back to the same move, made at a different stage and with different people.

What I'd do on Monday

If you've read this far, here's what I'd do first thing next week. Take the list of names you've been building since the introduction. Pick one. Write them a short note about their work, what you admire about it and one question you'd love to ask them. Invite them to talk, on a show if you have one or on a call if you don't.

Prepare for that conversation as if it were the most important meeting of your month. Ask your question, then listen. When you're done, send them something useful. Then do it again with the next name.

It won't feel like strategy at first, and that's fine. A year of those conversations will teach you more about your market than any report, and it'll leave you with relationships that open doors you couldn't have knocked on.

A thank you

This book belongs to my guests. They came on the show, spoke honestly about what worked and what didn't, and let me share their words. Every quote in these pages came from a live taping, and every one is attributed. If a line helped you, go find that guest and tell them. It's the kind of small gift that makes this whole approach work.

I'll keep asking questions on The Sunny Ray Show, and I'd love to hear what you build with these ideas. When you're ready, maybe you'll come sit in the chair across from me and tell me your story. What will it be?

Part 07Sources

Chapter 11Where every quote came from

Every quotation in this book is a guest's own words from a live taping of The Sunny Ray Show, checked against the transcript of that episode. Guests are listed with the date of the taping.

• "Some of my investors in both companies were people that I met hosting my podcast" Aviv Frankel, Shuttlebase, 2026-10-21
• "why is there a line at the printer every single day?" Graham Topol, MGT Insurance, 2026-10-23
• "You open a bakery because you love to bake" Graham Topol, MGT Insurance, 2026-10-23
• "trying to find a solution to that, like how to send money back to Argentina, is how I found Bitcoin" Sebastian Serrano, Ripio, 2026-10-13
• "so busy solving a cool tech problem" Madhukar Bhatia, Pentathlon Ventures, 2026-10-19
• "Do you understand the market that you're going to serve, and do you have any unique insight?" Madhukar Bhatia, Pentathlon Ventures, 2026-10-19
• "code has absolutely zero value. Software has zero value" Jorge Alcantara, Zentrick, 2026-09-07
• "IP is only as good as your ability to commercialize the IP" Luca Pandolfi, Woodland Bio, 2026-10-30
• "you don't know what you don't know" Mitchell Clarke, 2026-10-08
• "you gotta be prepared to make an investment for 10 years" Mick Kanfi, Earth Collective, 2026-10-14
• "you just start and you learn on the job" Sam Kamani, Web3 Pod, 2026-10-23
• "a lack of options provides clarity" Jim Donnelly, 2026-09-10
• "It put investors in front of me. Some of my investors in both companies were people that I met hosting my podcast" Aviv Frankel, Shuttlebase, 2026-10-21
• "on my show they're not pitching to a VC" Sam Kamani, Web3 Pod, 2026-10-23
• "you take the time to talk with people and really listen" Reagan Rodriguez, 2026-09-08
• "the most important thing you can do as a founder is to talk to your prospective customers" Shikha Miglani, Saarthee, 2026-10-16
• "I'm not looking for the audience. I'm looking for, you know, to build a network" Yaniv Feldman, Flag Capital, 2026-10-20
• "It almost always starts offline" Tim Hayden, Brain+Trust, 2026-10-19
• "They die for a lack of customers" Mike Ma, Sidecut Ventures, 2026-10-30
• "before I spent the time on engineering or the solution on any technology side, I had 3 MOUs signed with clients that were gonna use the technology" Sameer Pirani, Brinc, 2026-10-21
• "thinking that if I build something great, people are just gonna come to it" Sameer Pirani, Brinc, 2026-10-21
• "already knew my work and trusted our technical expertise" Robin Park, Chaparral Labs, 2026-10-15
• "by the end of that gig, I've designed a platform that they really liked and they said, could you build it for us?" Natalie Kaminski, JetRockets, 2026-10-08
• "because we'd built trust with them" Marlon Tesla, Tesla Solutions, 2026-10-26
• "For a while, we wanted to be the everything company for the everything brand for everyone" Christian Brown, Glewee, 2026-10-30
• "When we first found really good success, it was when we started niching down" Christian Brown, Glewee, 2026-10-30
• "you can't as a small startup, you can't serve every single vertical in your market at the beginning" Ajay Bam, Vyral, 2026-09-02
• "initially we started with mid-market before moving to enterprise" Chetan Saundankar, Coditation, 2026-09-21
• "begging our friends to take the $50 deal for the Instagram story just to prove it worked" Christian Brown, Glewee, 2026-10-30
• "As I started doing founder-led sales, like, wow, sales is really challenging" Pianpian Guthrie, Amotions, 2026-09-11
• "after two months, the CTO called me back" Shivoh Chirayil Nandakumar, RideScan AI, 2026-10-27
• "they paid upfront" Shivoh Chirayil Nandakumar, RideScan AI, 2026-10-27
• "you put your understanding of people to the test every day" Karin Stephan, Sidekick, 2026-10-26
• "It's hard to fake your way through 30 days of watching go-to-market" Mike Ma, Sidecut Ventures, 2026-10-30
• "That one post got 100,000 views and over 200 DMs" Jarrett Thomas, More Than Media, 2026-10-09
• "on day 89, I ended up closing a deal for $450,000 a week before the pandemic" Jarrett Thomas, More Than Media, 2026-10-09
• "Anything that you post should make somebody feel something, even if it's about business" Jarrett Thomas, More Than Media, 2026-10-09
• "We don't have to guess what your customers are going to chat with the internet about because they literally chatted to your people at the front" Joe Toscano, Service Stories, 2026-09-02
• "I actually don't try to sell AI. I try to sell outcomes" Joe Toscano, Service Stories, 2026-09-02
• "what exactly this is and who exactly this is for" Mariya Pallais, Pinkfins, 2026-10-07
• "our close rate is like 80%, 90%" Mariya Pallais, Pinkfins, 2026-10-07
• "taking these insights" Itay Kahana, Watchful, 2026-10-28
• "It was very difficult and it was a mistake when I'm thinking about it" Itay Kahana, Watchful, 2026-10-28
• "we have relationships with a lot of publishers of these newsletters" David Gompert, Avant-Garde Trading, 2026-10-20
• "I think 8 weeks later, we delivered the full system" Stuart Frost, Geminos, 2026-10-27
• "every train company in the UK has that same problem. So we're now selling to all of them" Stuart Frost, Geminos, 2026-10-27
• "All of that's go-to-market related problems" Parag Vaish, NextNow, 2026-10-30
• "First of all, I led with data. So I didn't just give them a pitch and like did a very generic pitch. I gave them data about the competition and stuff that they didn't know" Itay Kahana, Watchful, 2026-10-28
• "So maybe it was a too low number" Itay Kahana, Watchful, 2026-10-28
• "the only argument you can make is money, either on the bottom line or on the top line" Anders Teigland, 2026-10-30
• "I try to sell outcomes" Joe Toscano, Service Stories, 2026-09-02
• "you never want to be in a position where you're always the cheapest guy" Christopher Nelson, Alpha Hire, 2026-08-28
• "if you are not differentiated, you fight on price every single transaction" Yariv Adan, Ellipsis Venture, 2026-10-23
• "We choose not to sell fear to sell our products and services" Marlon Tesla, Tesla Solutions, 2026-10-26
• "Make it obvious for the person reading it" Maurice Harary, The Bid Lab, 2026-10-21
• "there's also a psychology to losing" Maurice Harary, The Bid Lab, 2026-10-21
• "just blown away" Stuart Frost, Geminos, 2026-10-27
• "usually when you build a relationship, the problem that they need to solve will always show itself" Jarrett Thomas, More Than Media, 2026-10-09
• "most of the times they don't even know that they are really good at sales" Sam Kamani, Web3 Pod, 2026-10-23
• "We tell them that they have to hit the whole investment or the funding conversation way before they even realize they need the money" Vaishali James, Sangatna Angels, 2026-10-13
• "It's not a rejection, just collect it as data" Vaishali James, Sangatna Angels, 2026-10-13
• "what asset are you writing? You're writing the founder" Mike Ma, Sidecut Ventures, 2026-10-30
• "the average time I'm on your cap table is a decade" Mike Ma, Sidecut Ventures, 2026-10-30
• "he tells you that he screwed up and here's what he's going to do to fix it. You know, that transparency is super important" Ed Lafferty, Saturn Partners, 2026-11-03
• "you shouldn't be focused on raising capital per se, but more on the adoption side" Sameer Pirani, Brinc, 2026-10-21
• "We're not investing in ideas. You got to have revenue and some kind of traction. You better know the industry you are in" Michel Friedman, Reflect Ventures, 2026-10-28
• "if an investor tells you that he's very confident that he can always pick winners, you don't want his money" Michel Friedman, Reflect Ventures, 2026-10-28
• "you don't want investors criticizing you at that moment instead of supporting you" Bernard Harguindeguy, Executive Venture Fund, 2026-10-29
• "they can make a phone call" Karl Clark, B.I.G. Intelligence AI, 2026-10-22
• "I'm going to raise money From people that I like, life is short" Jim Donnelly, 2026-09-10
• "a VC can't do anything with you" Yaniv Feldman, Flag Capital, 2026-10-20
• "wiped out 90% of the available investors immediately" Ken Deering, iGuard, 2026-10-20
• "capital is generally applied as a cash flow exercise" Gregg Bauer, ScaleUp Labs, 2026-10-26
• "won't touch a founder unless that founder has failed at least once" Gregg Bauer, ScaleUp Labs, 2026-10-26
• "One's gonna be like relationship and access to capital and one's gonna be like hyper expertise" Rachael Richardson, Florida Funders, 2026-10-29
• "staying separate from outside investor money allowed us to stay afloat long enough to find paying customers" Marlon Tesla, Tesla Solutions, 2026-10-26
• "He's that person that people trust" Luca Pandolfi, Woodland Bio, 2026-10-30
• "expenses are certain, revenues are uncertain" James Vanreusel, Vanreusel Ventures, 2026-10-20
• "impossible to really be qualified or ready to go when you first get it" Joel Trammell, Xpertloop, 2026-10-14
• "just because we had a bunch of smart people, it didn't mean the organization ran well" Joel Trammell, Xpertloop, 2026-10-14
• "I would definitely surround myself with more people that have been in the position that I want to be in at a much earlier stage" Sameer Pirani, Brinc, 2026-10-21
• "the only thing that can't be copied is your ability to capture the spirit of your people" Dave Clare, Circle Leadership, 2026-09-16
• "we should have resources for humans, not humans as a resource" Dave Clare, Circle Leadership, 2026-09-16
• "what kind of company do we want to work for?" Natalie Kaminski, JetRockets, 2026-10-08
• "empowering your team to talk to your customers without asking your permission" Ajay Bam, Vyral, 2026-09-02
• "you're empowering your team to criticize both your leadership and anyone in the company with respect" Ajay Bam, Vyral, 2026-09-02
• "So the decision ownership stays with the employee, and this is the core" Gordian, 2026-10-30
• "that first hire is so important to maintain and grow your culture or potentially implode it" Scott Finkelstein, Yutavis, 2026-10-30
• "the best place with the most amount of people was Reddit" Benton Calder, 2026-09-08
• "He found me. I made a post or 2 on Reddit" Addison Houston, Arbit Financial, 2026-11-02
• "So-called the communication contracts" Aleksandra Łoś, Relayn, 2026-11-03
• "instead of replacing my team, I should empower them and provide them with the AI tools they need to deliver" Aleksandar Hadzhiyski, Titan Agency, 2026-10-20
• "I decided in that moment of realizing I was alone to reach out to one of my mentors and reconnect with them" Scott Finkelstein, Yutavis, 2026-10-30
• "optimized for the demo but not for the real scale" Shivoh Chirayil Nandakumar, RideScan AI, 2026-10-27
• "an 87% failure rate to get from a demo to an actual production application" Stuart Frost, Geminos, 2026-10-27
• "To go from piloting into large-scale manufacturing is a whole different beast" Anders Teigland, 2026-10-30
• "building one of one thing is easy" Benton Calder, 2026-09-08
• "if you left the business for the next 6 months, you took a hiatus" Andy Harris, STS Capital Partners, 2026-09-24
• "do a sell-side quality of earnings ahead of time" Andy Harris, STS Capital Partners, 2026-09-24
• "Every one of the partnerships that you work with ultimately become a potential acquirer" Bernard Harguindeguy, Executive Venture Fund, 2026-10-29
• "almost every stockbroker that offers crypto in Argentina does it with us" Sebastian Serrano, Ripio, 2026-10-13
• "It's a 6-month slog, and they're going to be all kind of twists and turns" Joel Trammell, Xpertloop, 2026-10-14
• "a return is not real until the money is back into your account" Elisabeth Cabanas, 2026-09-03
• "Sometimes when you slow cook, the food is so yummy" Shikha Miglani, Saarthee, 2026-10-16
• "it's hard to beat a guy who never gives up" Nils Welin, ProGuard, 2026-09-03
• "Motivation fades. Discipline I can count on" Harvey Berman, 2026-09-24
• "a lack of options provides clarity" Jim Donnelly, 2026-09-10
• "I don't trust my gut anymore" Anthony Vinci, Vico, 2026-10-21
• "If you're a real estate company, you will be a Bitcoin company" Leon Wankum, oneVest, 2026-10-15