What 100 VC Fast Pitch Events Taught Scott Kelly

What we talked about.

Sunny Ray sits down with Scott Kelly, founder and CEO of Black Dog Venture Partners and host of VC Fast Pitch, to unpack lessons from 15 years and nearly 100 pitch events. Kelly traces his path from the floor of the New York Stock Exchange in the early 1980s through investment banking, three exited internet companies, and building sales and PR teams before launching Black Dog. He shares why he democratized his pitch events while quietly vetting the investors in the room, warns founders against claiming no competition or chasing hype, and stresses that team execution matters more than raw ideas. Kelly explains his current headline philosophy, don't raise, build, describing how he helps founders assess whether bootstrapping, direct sales, or capital raising fits their stage. He also discusses expanding events internationally, launching Investors and Innovators networking nights and the Emerging Managers podcast, and how AI is shrinking the capital founders actually need. Throughout, Kelly returns to relationships, culture, and due diligence on both sides of the table as the real differentiators in fundraising success.

A 35-year deal maker on why founders should build first, raise later, and vet investors as hard as investors vet them.

The questions, and the answers.

What is Black Dog Venture Partners at a high level?

I've been a deal guy for 35 years, starting on the NYSE floor in the early 80s, then investment banking taking tech companies public until 93, then founding and exiting three internet companies in the 90s. After a brief retirement I started Black Dog Venture Partners, working with early stage founders to fund, scale, and eventually exit their business, including through our VC Fast Pitch events, which we've hosted for 15 years.

After 15 years and close to a thousand companies presenting, what's the common denominator you see founders get wrong?

We do exactly five-minute pitches, and the common denominator is boiling down the essentials investors want: what's the problem and why is it worth solving, what's your solution and why is it better, how do you make money, who are your customers, who's on your team and why they can execute, how much you're raising, and what milestones you'll hit with that capital.

What was the first business you tried to raise money for, and what did it teach you?

My lemonade stand at age 11, raising seed capital from my mom. Later, after a successful investment banking career, I came home one Friday, told my wife I was quitting, and by Monday started an internet fintech company out of my spare bedroom. I raised a little capital and exited a few years later. Once you do it once, you're hooked.

What's the biggest difference between how a great salesperson pitches and how a great founder pitches?

The ability to sell has become a lost art with digital marketing taking over actual face-to-face asks for money. Sales begins with solving a problem for the other person, not for you. With investors, you have to understand investor math, many VC firms lose 100% on plenty of investments, and you need to convince them why you're not one of those, by telling a story that inspires them.

What's the most common reason a genuinely good company fails to raise, aside from opportunity size?

Founders say things that don't impress investors, like claiming they have no competition, when the pencil is still competition to the computer. Others make bold claims like just getting 1% of the market makes them a trillion-dollar company instead of being pragmatic. Founders also often fail to build a proper team around their technical skills, and investors weigh team and execution heavily.

If you had to redesign VC Fast Pitch from scratch today, what would you build differently?

We're actually doing this now, using AI and other tools to scale and more effectively get entrepreneurs in front of a larger group of investors. The event has been very successful with great stories, but we have to be aware of the technology out there. I'm big on personal relationships, so the goal is being more technically savvy while still connecting the right entrepreneur to the right investors.

Your headline message is 'don't raise, build.' How do you reconcile that with your career helping founders raise capital?

The irony is 98 to 99% of entrepreneurs shouldn't even pursue venture capital. Raising capital is a full-time job that takes your eye off building the business, and taking money means gaining an opinion you may not want. We had a company raising $2 million that we instead helped sell $2 million of product, so they got sales instead of dilution.

Does AI change the calculus on how much capital a company actually needs?

Absolutely, and it's already happening. Less than a couple of years ago you needed a whole development team to build a tech product. Now you can build that tech stack with far fewer people and a much smaller budget, so use of proceeds doesn't have to mean hiring 50 to 100 developers anymore.