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:

1. Why Weebly stayed cash flow positive from early 2009 and what that meant for how they built the company
2. How David thinks about dilution — and why inefficient spending is where founders actually lose equity
3. The three headcount breaking points every CEO hits and how your role has to change at each one
4. Why small businesses need owned channels and how marketplaces eating their margin is the defining tension in that market
5. What clean tech investing looked like during the Vinod Khosla era vs. how David approaches it now
6. Why solar's cost curve looks nothing like oil's over the last 100 years — and what that means for timing
7. How David thinks about nuclear's role alongside renewables
8. What made the Weebly acquisition to Square work when most acquisitions don't
9. How word of mouth drove 80%+ of Weebly's growth and why that's hard to explain to investors
10. 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