Fast Five Friday: Ways to raise from strength

Hi,

Welcome to Bankrolling Tomorrow - your no‑BS guide to raise capital.

It’s the second weekend of the first month of 2026, and as you can see, I’ve started drinking coffee again.  

Good week on my end: still productive, marathon training is back on, reading more, writing more, and returning to my deeply questionable routine of caffeine and raw eggs (not at the same time, or maybe at the same time - who knows)?

Founders do things uniquely - I’m hardly special there (I am, but in my own way).

This week’s case is a great example: Sam Parr. He went from shouting “ALL BEEF!” at a Nashville hot‑dog stand pulling smart people into an Anti‑MBA book club, then spinning that network into HustleCon - a scrappy, profitable conference that proved he could acquire customers and monetise an audience fast. That pattern mattered later.

Then came The Hustle. He used HustleCon profits plus a small cheque to launch a daily business email that felt human, not corporate. It became a morning habit for 1M+ readers, then expanded into Trends, a paid research/community that showed the audience would pay - not just click. By the time buyers came knocking, he’d raised modestly, kept control, and - most importantly - owned distribution. HubSpot didn’t buy fancy tech; they bought trust and attention at scale.

If you want the full play‑by‑play behind how he raised from strength (not panic) and why the deal made sense, the deep dive is here. 

But for skimmers, here are 5 things you can take from The Hustle’s capital raise, and apply to your business today:

1/ Create momentum with small, fast bets.
Sam didn’t wait for a perfect plan. He ran an Anti‑MBA book club that built a founder/investor network, co-founded Bunk and sold it quickly (small exit, but it bought him time), then turned a 300‑person list into HustleCon - profitable in six weeks. Those scrappy reps proved he could find demand, get attention, and monetise it.

2/ Let customers validate; only raise to scale.
Each step was funded by revenue first. HustleCon profits plus a modest $250k check kicked off The Hustle. He didn’t touch paid growth until 250k organic subscribers and clear unit economics. When he tested Trends, a Gum road presale did ~$30k in 24 hours; launch hit ~$1.2M ARR with 4,000 members - proof people would pay before he poured fuel on it.

3/ Own distribution - the asset acquirers pay for.
Turning The Hustle into a daily email made it a habit for 1-2 million readers. That trust and attention became the real moat. When HubSpot wanted to expand “HubSpot Media,” they weren’t buying novel tech - they were buying a direct line to a perfectly matched audience, every morning.

4/ Keep the rounds light to keep control.
Across the journey he raised a low seven‑figure total, intentionally. Smaller, timed raises preserved equity and optionality, avoided the growth‑at‑all‑costs treadmill, and let him choose the outcome. When acquisition talks started, he could be blunt and transparent because he wasn’t over‑funded or over‑promised.

5/ De‑risk in sequence - and know your math cold.
Each move sets up the next: Bunk - salary/time; HustleCon - cash flow + list; The Hustle - brand + scale; Trends - paid validation. He scaled spend only when LTV, CAC, and payback were understood, turning growth into a math problem instead of a gamble.

That’s the game: stack small wins, let revenue prove it, then raise on your terms. Pick one move you can ship this week - tiny is fine - and tell me what you chose.

Thanks for allowing me into your inbox every week.

If you have any questions, or want to discuss any of my rants on these topics in depth, reply to this email, and I will get back to you ASAP.

Talk soon,

James