From Personal Checks to Fund I: Thesis and Fundraising

Grant Hensel has started 10 companies (7 failed, 2 sold, 1 scaled), bought a business his wife now operates, and then got obsessed with backing self-funded searchers. He’s the founder of Entrepreneurial Capital, raising ~$11M to invest in “cockroach” SMBs at 3–5x earnings alongside gritty owner-operators.

If you’re buying or backing boring, profitable businesses, this is a playbook episode.

CapitalPad: the SMB investment platform for accredited investors & searchers. Join now: https://capitalpad.com/ (Not investment advice.)

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You'll learn:
00:00 Grant’s path: 10 starts, 2 exits, 1 scaled; now backing self-funded searchers
00:32 Grant’s background & living the “buy vs. build” debate
02:26 Buying a business for his wife to run (4 LOIs, funny diligence misses)
05:24 First 90 days: installing EOS, weekly scorecard, real traction
06:52 Portfolio before the fund (one built, one bought)
07:08 Sponsor — Capitalbat (SMB investor ↔︎ searcher platform)
07:59 Holdco vs. minority investing; why operator quality dominates
09:32 Why self-funded search is a built-in grit test
10:14 From personal checks to raising a fund (organic evolution)
12:23 The four screens: low concentration, low capex, low cyclicality, history of profits
13:53 Cyclicality lesson: cheap isn’t worth macro sensitivity
15:52 Fund timeline: Oct ’24 idea → Feb ’25 start → Jul ’25 close
16:39 Fundraising tactics: “ask for advice,” webinars, soft-circle snowball
18:41 Sponsor — SpaceBar Studios (done-for-you newsletters)
20:27 Looking at deals while raising; confidence once ~$5M soft-circled
21:16 How Grant picks winners: on-site diligence, non-spreadsheet reality
22:51 Sourcing searchers: Searcher.com, webinars, “This Week in ETA” newsletter
26:15 Day-to-day now: LOI diligence, marketing, advisor feedback (pre-first deal)
27:17 Deployment pace: 13–18 deals over 2–3 years (~1 every other month)
27:38 Deal flow volume: ~1 LOI/day; be ultra-selective
28:03 The five pre-LOI seller questions (and why they matter)
32:26 What to buy (and avoid): home/B2B services, light mfg (with chops); no e-comm/retail/restaurants
33:58 The real investor value-add: resilience through the ugly middle
35:18 Roll-up skepticism; single-asset cash flow is better than multiple-expansion bets
37:53 First-90-days playbook: live in the trenches; avoid “academic” fixes
39:45 Inventory cautionary tale: don’t break the value prop you can’t see on a P&L
44:19 Game-changer hire: Chief of Staff as force multiplier
46:10 Failure as teacher; base rates favor buying over building
48:23 Where to find Grant (Twitter & LinkedIn)
49:05 Favorites: Switch, Good to Great, Traction; best advice—circle of competence
50:51 Wrap-up & close

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This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.