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Episode Summary
You’re staring at your first term sheet. Three pages of words you don’t know. Liquidation preferences. Drag-alongs. Three-X preference. The guy across the table tells you it’s just market, take it or leave it, and if you walk away you’ll never raise money again. That’s where Sarah Dusek sat in 2017 with Under Canvas, the glamping company she pioneered out of Bozeman with her husband. She turned down $7M, cried in front of her team, told them they might run out of cash, and went and raised $17M from a partner who actually cared about the business. A year later she sold a majority to private equity. And only after the close did she learn the PE playbook is basically property development: buy it, paint it, flip it in five to seven years. In this conversation, Sarah and I got into how she went from not knowing what EBITDA was to a nine-figure exit, why only 2% of women raise venture capital and why it’s an information asymmetry problem more than a network problem, what she’d do differently in the PE conversation, and why she started Enigma Ventures to invest in women-led businesses in Southern Africa.
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## Top 10 Takeaways- Nobody starts a business to sell a business. You start one to solve a problem, and the capital question comes years later.
- Your brand is worth more than your product. Selling the tent would have killed Under Canvas.
- EBITDA is the language investors speak. Not knowing it costs you choices at the table.
- Venture capital wants 10x on capital. Knowing their math lets you decide if your business actually fits theirs.
- There is no such thing as “just market.” Every term sheet is negotiable, and the people telling you otherwise are selling you.
- If the partnership feels like bullying before the close, you already know how it ends.
- Capital is oxygen for growth, and the blend of debt and equity defines what you give up to get it.
- If you’re not in the club, find the broker who is. Networks raise capital, not pitch decks.
- Private equity has a playbook: small tweaks, margin lift, flip in five to seven years. Know it before you sign.
- The information asymmetry at close is not on your side. Where the money flows, the power flows, and your liquidity event decides what gets built next.
Sound Bites
“Nobody really ever goes into business to sell a business. You go into business to solve a problem.” (@TBD) — Sarah Dusek
“She explained EBITDA to me for the first time ever. Suddenly understood that there was a metric, a financial metric that was interesting to venture capitalists.” (@TBD) — Sarah Dusek
“I was told at that moment in time, if I didn’t do that deal, I would get blacklisted and I would never raise money from anyone because they would put the word out that I was not playing by the rules.” (@TBD) — Sarah Dusek
“I wish I had known they had a playbook. They have a very clear playbook. For all intents and purposes, they’re like property developers. You redo the house, you put some makeup on the house and you flip it.” (@TBD) — Sarah Dusek
“It’s like the mindset shift where you go from solving for annual income and organic growth to what is EBITDA multiples. It’s like seeing the zeros and ones in the matrix.” (@TBD) — Ryan Tansom
About This Episode
Sarah Dusek is the co-founder of Under Canvas, the largest glamping company in the United States, which she and her husband Jake started in Bozeman, Montana in 2009. Sarah was named an EY Entrepreneurial Winning Woman, and Under Canvas landed on the Inc. 5000 before selling a majority stake to private equity in 2018. After the exit, Sarah moved to Southern Africa and founded Enigma Ventures, a venture capital fund focused on investing in women-led businesses on the continent. She is one of the 2% of female founders who has successfully raised institutional capital, and she is now on the other side of the table, trying to fix the asymmetry she lived through.
Resources Mentioned
- Under Canvas — The glamping company Sarah co-founded. — undercanvas.com
- Enigma Ventures — Sarah’s venture capital fund investing in women-led businesses in Southern Africa. — enigmaventures.com
- SBJ Capital — The California-based debt and equity partner that closed the $17M round with Under Canvas after she turned down the first offer.
- EY Entrepreneurial Winning Women — The Ernst & Young program where Ryan and Sarah first met.
- The Changing World Order by Ray Dalio — Referenced for the long-term debt cycle framing.
- The Prosperity Paradox — Referenced for the conscious-capitalism thesis on investment driving ecosystem-level value.
- All the President’s Bankers — Referenced for the long arc of who actually holds power inside the capital system.
Connections
Phase + Module:
- Module 2 — Expand Knowledge — Understanding valuation, capital structure, and the private capital playbook before you sit at the table
- Module 1 — Ownership Goals — Aligning the exit event with the original why
Milestones:
- Milestone 6 — Transaction Value — What a buyer actually pays, and what the structure does to your outcome
- Milestone 5 — Market Value — How the market prices your business depending on the buyer pool
- Milestone 4 — Owner’s Value (DCF) — The owner’s view of value before anyone else tells you what it’s worth
Concepts referenced:
- Normalized EBITDA — The metric Sarah didn’t know existed until a stranger explained it
- The Multiple & WACC — Why a 10x VC math problem looks different from a strategic buyer’s math
- Enterprise Value vs. Equity Value — The gap between the headline number and what lands in your account
- Value Gap — The space between what you think the business is worth and what the market will pay
- The Four Value Levers — Brand, growth, margin, and risk as the levers that priced Under Canvas
- Three Lenses of Value — Owner, market, and transaction — the three numbers Sarah was learning in real time