I Raised $11.7M To Back 13 Self-Funded Searchers | Grant Hensel Interview

Sep 20, 2025

Grant Hensel, founder of Entrepreneurial Capital, has an impressive entrepreneurial background with ten startups, including seven failures but also two successful exits. He dives into his passion for backing self-funded searchers and discusses his unique investment criteria focused on resilient SMBs. Grant shares hilarious anecdotes from buying a marketing agency for his wife, insights on the importance of operator quality, and why he believes self-funded search is a true grit test. Tune in for his thoughts on finding searchers and his post-acquisition playbook!

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ANECDOTE

Serial Founder Turned Buyer

Grant started 10 companies: seven failed, two sold, and one scaled to ~60 employees.
Buying a business his wife runs taught him he prefers backing operators to founding new tech startups.

ANECDOTE

Buying Through Trial And Error

Grant and his wife submitted four LOIs and bought a marketing agency found on Flippa after two deals fell for odd reasons.
His wife now runs the acquired agency, where implementing EOS created early traction.

ADVICE

Install An Operating System Fast

Implement EOS or a simple operating system immediately to align leadership and track weekly metrics.
Assign owners for 7–12 metrics and run a weekly leadership meeting to gain traction fast.

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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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