Braden, co-founder and CEO of Slash Experts, joins Sunny Ray to trace his path from a Chico, California upbringing surrounded by small business owner parents to building Sendoso into a $200 million category leader in B2B gifting. He recounts starting with Coffee Center, sending Starbucks gift cards before cadence tools existed, and even getting a cease and desist from Starbucks over unauthorized bulk gift card purchases. Braden reflects on the reciprocity behind gifting, the chaos of scaling too fast during COVID, and the leadership lessons learned from mismanaging a growing team. He explains why he walked away from Sendoso after a decade to found Slash Experts in 2024, betting that buyers trust other buyers more than any sales pitch. The conversation covers the loneliness of starting over, how AI has accelerated startup building, hiring philosophy shifts, and the origin of Slash Experts from watching customer dinners manually manufacture trust between prospects and existing users. Throughout, Braden emphasizes human connection over pure scale as his guiding principle.
Sendoso's co-founder on why he left his $200M gifting company to bet on buyer to buyer trust.
Can you tell me a little bit about Slash Experts?
The thesis of Slash Experts is that people like to buy from people. When you're going through a sales process as a prospect, we use AI to connect you with existing customers who look like you so you can chat with them. You ask things like would you buy it again, what should I have asked, what are you paying. Most folks love back channels, so we make it easy as experts.
What did sending people coffee teach you about what actually makes a human say yes?
Around 2014, 2015, cadence tools barely existed and outreach was generic, so we put a Starbucks gift card in the email with a pitch like grab a coffee on me. People stopped deleting the email right away and at least responded, even if just to say thanks. It stood out against the fifteen or twenty cold emails everyone got daily, and it opened the door a little.
A lot of founders chase scale. You seem wired toward connection and gratitude instead. Where did that wiring come from?
I always liked the relationship sale, which came from how I was raised with my parents running small businesses in a small town, where you knew your customer and built the relationship. Gifting made that easy. Sending something before a conversation changes the dynamic and makes you appear more human, which matters in a world of digital Zoom calls.
What's a moment early on where you were genuinely scared and did the thing anyway?
We were buying Starbucks gift cards straight off their website without any approval, pulling codes into a CSV for our cadences. We scaled it so much that Starbucks sent us a cease and desist over roughly sixty grand in cards. We thought we were too small to matter, but they cared. We ended up pitching them in Seattle, and that early conversation is still why we can send Starbucks cards today.
Take me to the moment you knew gifting was going to be enormous.
We had early product market fit because when we asked prospects if they did holiday gifting, everyone said yes, but nobody tracked whether it actually helped close deals or renewals. We pitched automating and tracking gifting in the CRM for the first time, which sold fast. Then COVID hit and everyone stuck at home wanted to send swag and wine to customers and employees, and growth exploded from there.
Scaling that fast breaks most people at least once. When did it nearly break you?
My job changed too fast, going from managing a handful of salespeople to a huge team without the right structure. My style was more hands off, set the goal and check in later, which doesn't work when people need career conversations, all hands meetings, and clear mission and values. We didn't build any of that for about a year, and it broke a lot of us.
What does it actually take to walk away from your own success?
There were times during our 2022 layoffs when I wanted out but pushed through with my co-founder and team. The real moment came once the company was profitable and growing after some acquisitions, and I realized I couldn't offer more than I had over the past ten years. I knew I had another company in me, so I decided to go build one more time.
When did you first feel in your gut that buyers trust other buyers more than any pitch?
It came from watching customer dinners, where you seat a happy customer next to a prospect hoping they'll reference you in real time. That works but doesn't scale and dinners are expensive. I realized about seventy percent of a deal happens before someone even requests a demo, through word of mouth and reviews, so why not scale that customer conversation with a tool instead of a dinner table.
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