What does Elbow Grease look for in a founder?

I spent a decade as a professional gambler before I started investing. First poker, then daily fantasy sports on sites like DraftKings and FanDuel. I always operated at a profit, because I had a team depending on me and payroll to make. It's an unusual background for someone who now runs a venture fund, but it taught me something I use every time I meet a founder: the person who's going to win isn't the one with the best résumé. It's the one who's already all in, who's been grinding on the problem long before anyone was paying them to.

That's the lens I bring to Elbow Grease. So when people ask what I actually look for in a founder, my honest answer is I'm looking for someone doing their life's work, solving a big problem they understand, who would keep building this company whether or not I ever wrote them a check.

The one question I always ask myself

Before I ask a founder anything else, I'm asking myself one thing: is this their life's work? Not a side project, not an idea they're testing to see if it sticks. If someone is doing their life's work and solving a big problem they understand, we want to know about it. When I meet a founder and I can tell they're going to build this thing with or without me, that's when I start paying attention.

I'm not looking for pedigree

Our founders tend to look a little different than the founders who are popular at a lot of other funds. I do not need to know if someone worked at a major consulting firm or investment bank to know if they are good or not. I am not looking for someone with a famous father, or a Big Tech executive who leaves their job with a blank check to go figure out what to build. In my experience, that story just doesn't end as well as people expect.

What I'm actually looking for:

• Scrappiness with something to show for it. You've demonstrated a lot with very little, such as a working product or a first customer. You have real proof you can execute without waiting for permission or funding.

• Full-time commitment. You've already quit your job. I want to see people who've decided before we ever get involved.

• Pre-seed software. You're building the first real version of something for real customers.

I made every mistake in the book building my own software company. I don't need someone with a clean résumé, I need someone who's already in the fight.

I'm looking for founders who know a secret

The founders I get most excited about have learned something about their problem that most people don't know, and they learned it the hard way. That might be from where they grew up, from a job they held for years, from a lived experience nobody can hand you. Dan jokes that when a pitch is really good, he wants to call his mother and tell her about it. It's usually because the founder has found an insight that feels like a secret, and once they realize it, they can't stop thinking about it. They're possessed by it.

That's very different than a polished pitch deck. Easy ideas and low-hanging fruit are already taken. We don’t want the easy or obvious problems. I want the founder who understands their problem because they've lived it.

I want problems that matter to real people

I think about this in terms of what founders need today. AI has made it cheaper and faster than ever to build a basic product and land your first customers, which means scrappy, driven founders don't need a big venture check just to get started. What they need is help with the parts that are genuinely hard. This is typically finding product-market fit, learning to recruit, and knowing what good looks like. I'm looking for founders solving problems that are big enough, and real enough, that they justify that kind of hands-on partnership. Companies of consequence, not companies chasing whatever's trending this quarter.

How I actually get to know someone

Here's what I want to know when I sit down with a founder: how much time are they spending with their target customers, and what are they learning from them? That tells me more than almost anything else. Founders who can talk specifically, not generally, about what their customers need and why, are usually the ones closest to actually finding product-market fit.

One thing that stuck with me from our first cohort. Ryan Denehy, CEO of Electric AI who was a mentor and hosted a lunch with cohort one, told me he noticed a through-line across the whole batch: no crazy egos. Just founders who showed up focused on the work. That's exactly the attitude I'm selecting for, as much as any individual metric I could give you.

What I'm not looking for

• A side project. I want founders who've already left their jobs to build full-time.

• A great fundraising pitch. Elbow Grease isn't a demo-day factory. I care much more about whether you understand your customer than whether you can work a room.

• Prestige as a stand-in for conviction. A big-name résumé doesn't move me. Evidence of drive does.

• An idea without a founder committed to it for the long haul. I'm evaluating people I want to support for years, not months.

  
  

Why I screen this way

Most accelerators are built around one outcome: get you fundraising-ready by demo day, then hand you off to someone else. That's not what we're doing. My hope is not that a founder leaves Elbow Grease at the end of ten weeks. My hope is that they stay. So long as you're devoting your career to building your company, I want to be part of it, and I want to keep investing. It's our ambition to be the only substantial capital partner a company needs before its Series A.

I only want to make that kind of commitment to the right founder. I'm not selecting for who can raise the most money the fastest. I'm selecting for who I want to build with for the next decade.

Questions I get asked a lot

Do you need a working product to apply?

No, but I want to see evidence of momentum, something you've built or shipped that shows you can execute with limited resources.

Do you fund founders outside of software?

Elbow Grease is primarily focused on pre-seed software companies. That said, Gutter's portfolio spans all industries and if you have a hardware solution, we encourage you to apply and if you believe that is the best solution for the problem, I want to hear about it.

Do you favor founders with experience working in startups?

No. Startup experience isn't what I'm screening for. Almost all of our founders are first-time founders. I want demonstrated drive and hard-earned understanding of the problem over an impressive résumé.

What does "doing your life's work" actually mean to you?

It means you're solving a problem you understand deeply, usually because of something personal or professional you lived through, and you're committed to it whether or not you ever raise outside capital.

Do I need to already be full-time on my startup to apply?

In most cases, yes. I'm looking for founders who have already quit their jobs and are building full-time.  We understand that some people may have personal circumstances that make it impossible to do this, but we expect to see a lot of demonstrated traction and commitment in any case.

What happens after the 10-week program?

I don't think of Elbow Grease as a graduation event. It's the first step in what I hope is a much longer relationship. My goal is to keep investing in companies that hit their milestones, and to be a founder's primary capital partner through pre-seed and into their seed round.

How to apply

The program runs 10 weeks on-site at our office on Canal Street in Chinatown, starting September 15. Every company that joins gets a $300k investment from us. 

If you're doing your life's work and solving a big problem you understand, I want to know about it. Elbow Grease's second cohort is now accepting applications through July 31. Learn more at elbowgrease.cc and apply at https://forms.gutter.cc/eg0002-application