Founders in Arms The Long Game: David Rusenko on Building Weebly, Surviving Acquisitions, and Investing in Climate
David Rusenko is the founder and CEO of Leap Forward Ventures, a pre-seed and seed climate tech fund investing in energy, deep tech, and the reinvention of industrial processes. Before that, he spent 14 years as co-founder and CEO of Weebly, growing it from a college project to a platform serving tens of millions of small businesses before selling to Square in 2018.
What you'll learn:
- Why Weebly stayed cash flow positive from early 2009 and what that meant for how they built the company
- How David thinks about dilution — and why inefficient spending is where founders actually lose equity
- The three headcount breaking points every CEO hits and how your role has to change at each one
- Why small businesses need owned channels and how marketplaces eating their margin is the defining tension in that market
- What clean tech investing looked like during the Vinod Khosla era vs. how David approaches it now
- Why solar's cost curve looks nothing like oil's over the last 100 years — and what that means for timing
- How David thinks about nuclear's role alongside renewables
- What made the Weebly acquisition to Square work when most acquisitions don't
- How word of mouth drove 80%+ of Weebly's growth and why that's hard to explain to investors
- Why David moved from operating to investing — and what the coach-on-the-sidelines framing means to him
In this episode, we cover:
(00:00) Cash flow positivity and dilution
(01:08) Introduction to David Rusenko and Leap Forward Ventures
(04:11) What Leap Forward Ventures invests in
(05:32) Why climate tech goes through investment cycles
(07:09) Oil price vs. solar cost curves over 100 years
(09:08) Clean tech timing and the dot-com parallel
(10:31) David's take on nuclear energy
(12:29) Why David moved from operating to investing
(13:45) Reflections on the Weebly acquisition
(15:13) The small business owned channel problem
(17:57) CEO breaking points at 25, 75, and 175 people
(20:02) What happens to your jokes at 75 employees
(22:55) Designing culture intentionally as you scale
(28:18) Keeping politics out of your organization
(32:50) Weebly's lowest points and near-death moments
(37:27) Bootstrapping vs. VC — David's actual view
(40:18) How Weebly grew: mostly word of mouth
(43:04) The three phases of an S-curve market
(44:13) What made the Square acquisition work
(48:30) Rapid fire