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Banana Costume Fundraising Tips with Ethan Austin from Outside Ventures | Alone Together | Ep. 10
"I just keep showing more and more of me until they either invest or say no.”
Banana Costume Fundraising Tips ... that was honestly what ChatGPT labeled the memory when I uploaded this podcast transcript, and I thought that was the absolute perfect name for this episode.
I’ve admired Ethan Austin, founder of Outside Ventures, ever since I was his Lyft driver out of Camp Hustle.
We had half the seatbelts we needed on the way back to SFO with some of my favorite people in venture — many of them already guests on this pod.Ethan has turned an unorthodox life path—law school, nonprofit founder, Techstars MD, solo GP—into a razor‑sharp perspective on backing “outsider” founders in climate and financial inclusion.
His secret weapon? Joy. The louder the banana costume, the clearer the signal that venture can—and maybe should—be fun.
All kidding aside, he's taken that from a successful Fund I to launching Fund II and there are so many gems in here for founders, other GPs, or aspiring angels. In this episode Ethan and I dig into:
- Why joy is a sourcing moat and how a goofy monthly LP update beats a glossy 30‑page PDF.
- The banana‑costume epiphany: running law‑school bake sales in full fruit regalia and realizing he’d never be the greatest lawyer—but could be the happiest VC.
- Firing an LP to reclaim headspace (and why “right capital” is better than “more capital”).
- Solo‑GP triage: letting non‑critical fires burn, leaning on LP specialists, and knowing when to stop diligencing and trust the gut.
- Authenticity at scale—posting kids’ photos, April‑Fools mergers with Banana Capital, and the power of repelling the wrong people so the right ones can find you.
Ethan’s story is a reminder that vulnerability isn’t a soft skill; it’s a sharp edge. I hope you listen with an open heart—and maybe a slice of banana bread.
---Chapters
00:00 Cramped‑car origin story & why this episode took 3 months to schedule
02:52 Outside Ventures 101: Fund II, $250-$750 k first checks, outsider thesis
04:48 Defining “outsider” (mindset, not résumé)
08:32 Childhood wanderlust, hostel plots, and chronic authority‑allergy
10:18 Losing Dad at 12 → “Have fun, do good, help others” operating system
13:58 The legendary banana‑costume fundraiser (full marathon + training runs)
18:43 Joy as competitive edge: founders remember fun
21:18 Monthly LP updates people actually read (Easter eggs included)
26:06 Authenticity online: kids, jokes, and LinkedIn vulnerability
30:11 Why Ethan puts the banana photo inside his Fund II deck
33:06 Saying “no thanks” to a stressful LP
35:56 Humor dial: knowing when to crank it to 11—or drop to 0
36:15 Lessons from Fund I: focus on three superpowers, let the rest smolder
41:40 Diligence in practice: off‑list calls, product play‑tests, LP brain‑trust
47:03 Art vs. science in pre‑seed: when to quit researching and pull the trigger
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By Sidecut Ventures"I just keep showing more and more of me until they either invest or say no.”
Banana Costume Fundraising Tips ... that was honestly what ChatGPT labeled the memory when I uploaded this podcast transcript, and I thought that was the absolute perfect name for this episode.
I’ve admired Ethan Austin, founder of Outside Ventures, ever since I was his Lyft driver out of Camp Hustle.
We had half the seatbelts we needed on the way back to SFO with some of my favorite people in venture — many of them already guests on this pod.Ethan has turned an unorthodox life path—law school, nonprofit founder, Techstars MD, solo GP—into a razor‑sharp perspective on backing “outsider” founders in climate and financial inclusion.
His secret weapon? Joy. The louder the banana costume, the clearer the signal that venture can—and maybe should—be fun.
All kidding aside, he's taken that from a successful Fund I to launching Fund II and there are so many gems in here for founders, other GPs, or aspiring angels. In this episode Ethan and I dig into:
- Why joy is a sourcing moat and how a goofy monthly LP update beats a glossy 30‑page PDF.
- The banana‑costume epiphany: running law‑school bake sales in full fruit regalia and realizing he’d never be the greatest lawyer—but could be the happiest VC.
- Firing an LP to reclaim headspace (and why “right capital” is better than “more capital”).
- Solo‑GP triage: letting non‑critical fires burn, leaning on LP specialists, and knowing when to stop diligencing and trust the gut.
- Authenticity at scale—posting kids’ photos, April‑Fools mergers with Banana Capital, and the power of repelling the wrong people so the right ones can find you.
Ethan’s story is a reminder that vulnerability isn’t a soft skill; it’s a sharp edge. I hope you listen with an open heart—and maybe a slice of banana bread.
---Chapters
00:00 Cramped‑car origin story & why this episode took 3 months to schedule
02:52 Outside Ventures 101: Fund II, $250-$750 k first checks, outsider thesis
04:48 Defining “outsider” (mindset, not résumé)
08:32 Childhood wanderlust, hostel plots, and chronic authority‑allergy
10:18 Losing Dad at 12 → “Have fun, do good, help others” operating system
13:58 The legendary banana‑costume fundraiser (full marathon + training runs)
18:43 Joy as competitive edge: founders remember fun
21:18 Monthly LP updates people actually read (Easter eggs included)
26:06 Authenticity online: kids, jokes, and LinkedIn vulnerability
30:11 Why Ethan puts the banana photo inside his Fund II deck
33:06 Saying “no thanks” to a stressful LP
35:56 Humor dial: knowing when to crank it to 11—or drop to 0
36:15 Lessons from Fund I: focus on three superpowers, let the rest smolder
41:40 Diligence in practice: off‑list calls, product play‑tests, LP brain‑trust
47:03 Art vs. science in pre‑seed: when to quit researching and pull the trigger