Sunny Ray sits down with Mike Ma, the solo general partner of Sidecut Ventures, to unpack an unusual underwriting model: a free 30 day coaching period that comes before any check is written. Mike explains why he sees the founder as the real asset, why decks and customer references can be faked, and why watching someone work on go-to-market in real time reveals far more than a resume. Drawing on a career that includes Betterment, Bank of America, Vanguard, and Sway Ventures, plus a stretch as an angel investor, he describes how the approach evolved and why Sidecut passes on roughly 40 percent of founders who finish the process. The conversation covers the Moneystack case study, traction benchmarks at pre-seed and seed, the danger of Rolodex sales, and what action oriented self awareness looks like in a first meeting. Mike also shares how Sidecut backs impact driven founders he calls go-to-market killers for good, how his small team supports the process, and how founders can apply through the firm's site.
Mike Ma coaches founders for 30 days before investing, because you can fake a deck but not a month of go-to-market.
Why coach founders for 30 days before writing a check, and what do you learn?
The only asset I'm really investing in is the founder. You can fake your way through a deck and two meetings, but it's hard to fake 30 days of go-to-market work. I don't want to watch film of you playing, I want to play ball with you. That's how I get conviction about who the founder really is.
At what point did you decide coaching had to come before the check, not after?
I wrote a lot of angel checks based on pedigree, other people's views, or left-brain go-to-market analysis, and some didn't work out. This business is about funding the carbon-based life form in front of you, with their hopes and fears. There's no spreadsheet for that. Resumes are the past, and real-time coaching is the best way to see today.
What did your angel investing teach you before you raised a fund?
Two things. If I did it again, I'd put half that money into other funds as an LP. And coaching as underwriting needs room for failure. We pass on 40% of founders who finish the 30 days. It's not a service where I'm trying to retain a customer. I give real value while also getting the signal that lets me say no.
Who was the first founder to prove the model works?
Alex DiMarco, CEO of Moneystack, whom I met at TechCrunch Disrupt. They build financial counseling for people with mental health problems, with problem gambling as the wedge. We worked hard on his ICP and landed on a B2G motion, selling into government problem gambling offices. Neither of us expected that, but he earned it, scaled it, and raised a graduated round.
What kind of revenue and traction do you look for?
It varies, but at pre-seed I'm looking for somewhere around high five to low six figure ARR. At seed, for a roughly $20 million post deal, I want seven figures. The key is proof you can sell to people you're not related to. Zero CAC from Rolodex sales is actually a negative for me, because you'll run out of contacts.
What does coachable mean when you size up a founder in the first meeting?
Action oriented self awareness. First, do you understand where you actually are in the world? Some founders are out of touch with reality. Second, do you do something with that awareness? Plenty of founders talk and talk. In our 30 days I keep saying, don't tell me, show me. In fact, show yourself.
What ties together a portfolio that spans health, education, climate, and fintech?
Two things. First, founders are go-to-market killers for good, meaning they're fighting some kind of evil in the world, and I live with them for 30 days to see if they live those morals. Second, they're voracious go-to-market fiends who wake up and go to bed thinking about how to get customers more efficiently.
How do founders find their way to Sidecut?
We're pretty prolific on LinkedIn, but the best way is our pitch page, where we publish our deal framework and what to expect in the 30 days. All deal flow, warm and cold, goes through that form. We ask two weird questions: what evil are you fighting, and who's the best coach you've ever had and why.
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