Investing in Big, Hard Problems

How do you underwrite pre-seed founders when the only durable asset is the human—before there’s product-market fit? In this episode, I go deep with Mike Ma, Managing Partner at Sidecut Ventures, on his 30-day “work-alongside” diligence, why he optimizes for action-oriented self-awareness, and how to calibrate coachability—especially in go-to-market—without overfitting to investor bias. We unpack earned secrets, impact theses in education, climate, healthcare, and economic mobility, solo-GP advantages, alignment pitfalls from 2021-era rounds, and the mindset habits he wishes he’d had earlier: “write at a fourth-grade level” and “document your screw-ups.”

Highlights:

• The 30-day “grind with them” model: watching founders operate to reduce storytelling bias.
• What predicts pre-seed survival: action-oriented self-awareness (execute fast and integrate feedback fast).
• Coachability, defined: focus on go-to-market (not deep tech) and respond to market-generated feedback.
• Earned secrets: the unfair advantage born at the intersection of novel markets + lived expertise.
• Why solo GPs can be more aligned: speed, conviction, and operator empathy at pre-seed.
• Valuation ≠ victory: how 2021-style prefs/marks can zero founders despite solid outcomes.
• Two habits for builders & investors: write simply and log your mistakes to kill self-deception.

Guest Bio:

Mike Ma is the Managing Partner of Sidecut Ventures, a pre-seed venture firm backing “coachable superheroes” in sectors including economic mobility, digital health, climate, and education. He brings a background as both an investor and operator, with prior roles that span venture capital, operating leadership, and company building. Before founding Sidecut, Mike held leadership positions at firms such as Sway Ventures and Nex Cubed, where he launched fintech initiatives and accelerator programs. He also served as a marketing leader at high-growth startups including Betterment and Own Up, and earlier in his career worked in brand strategy at major financial institutions. A graduate of Harvard University, Mike now applies his experience across investing, operations, and go-to-market strategy to help early-stage founders succeed.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mike Ma: https://www.linkedin.com/in/michaelwma/

Links Sidecut Ventures: https://www.sidecut.vc/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Preview (2:30) Assessing and predicting startup success (7:06) Coachability in startup founders (13:14) Market size misconceptions and value creation platforms (22:15) Solo GPs and early-stage startup advantages (24:14) Innovation and the AI startup landscape (25:35) Optionality and premium in early-stage funding (26:48) VC-startup alignment and second-order effects (29:22) Misalignment in funding and tragic outcomes (29:50) Thirty-day LLM project insights (30:41) Asymmetric information and bias in investing (33:20) Coaching founders and personal advice (36:57) Closing remarks