Harry Stebbings started 20VC in his bedroom at 18.
Ten years later: roughly 1,400 episodes, a $400M fund raised off the back of the show, and guests like Tim Ferriss and the co-CEO of Monday.com.
I respect the hustle. 20VC is one of the best interview podcasts ever built.
But here's my problem with it.
Half the episodes are about fund construction, LP dynamics, and whether a $400M seed fund can return 5x.
If you're a bootstrapped founder doing $10K MRR, none of that helps you ship this week.
You don't need to know how Coatue thinks about Perplexity. You need to know how a founder just like you got from $10K to $50K MRR.
So here are 8 podcasts like 20VC, ranked for founders who want the interview format they love, but with lessons they can actually use. I host the first one, and I'll be upfront about that.
1. Profitable Founder Podcast
Full disclosure: this one's mine.
I interview bootstrapped SaaS founders making $100K to $10M a year. 42 episodes and counting.
No VCs, no "state of venture" panels. Operators opening up their playbooks:
- A founder stuck at $25K/month with a bootstrapped CRM, and exactly how he got unstuck
- A solo founder making $3.5M/year with a LinkedIn AI agent
- A team that went from zero to $25K/month with one marketing channel
Every episode answers the same question: how did you actually do it? Real numbers, real channels, real pricing decisions.
I started the show because I was tired of founder interviews that stopped at "we focused on the customer." I sold my own SaaS after going from $15K to $75K a month, and the stuff that moved the needle was never in those vague interviews.
If 20VC is the view from the cap table, this is the view from the trenches.
2. My First Million
Shaan Puri and Sam Parr brainstorm business ideas every week.
Sam sold The Hustle to HubSpot. Shaan sold Bebo to Twitch. Both have done the thing, which is why the riffing works.
It's less "interview" than 20VC and more two smart friends spitballing. But the frameworks that come out of those conversations (the "$1M weekend business" breakdowns, the agency math, the content flywheels) are weirdly actionable.
Best for: idea generation when you're between projects, or when you want to steal a growth angle from another industry.
3. Acquired
Ben Gilbert and David Rosenthal spend 3 to 4 hours telling the full story of one company. Rolex. Costco. Hermès. NVIDIA.
It sounds like homework. It's not. It's the closest thing podcasting has to a prestige documentary series.
You won't get tactics for your Tuesday. You'll get pattern recognition: how moats actually form, why some companies compound for 50 years, what pricing power really looks like.
I wrote a full breakdown of podcasts like Acquired if the deep-dive format is your thing.
4. Lenny's Podcast
Lenny Rachitsky interviews product and growth leaders: the people who ran growth at Airbnb, Duolingo, Notion, Figma.
His newsletter has over 1,200,000 subscribers, and the podcast is the same muscle in audio form.
This is the show I'd pick if your bottleneck is product. Onboarding, activation, retention, pricing experiments: the guests have run these playbooks at scale and Lenny is good at pulling out the specifics.
Fair warning: most guests come from venture-backed companies, so filter the advice through your own constraints. "Hire a growth team" means something different at $20K MRR.
5. This Week in Startups
Jason Calacanis has been doing this since 2009. Angel investor in Uber and Robinhood, and one of the few hosts who will actually push back on a guest.
The format mixes startup news with founder and investor interviews, so it doubles as a way to stay current without doomscrolling X all day.
Of everything on this list, it's the closest to 20VC's energy: fast, opinionated, and plugged into every Silicon Valley rumor about a week before it goes public.
6. Invest Like the Best
Patrick O'Shaughnessy's show, part of his Colossus media company.
If what you love about 20VC is hearing brilliant investors explain how they think, this is the purest substitute. Patrick has interviewed hundreds of investors and operators, and he asks the kind of second-order questions Harry does on his best days.
It's broader than startups (public markets, private equity, media), which is exactly why it's useful. Some of my best SaaS pricing ideas came from hearing how investors in totally different asset classes think about value.
7. The Pitch
Real founders pitch real investors for real money, recorded in the room. Josh Muccio built it into what the show calls the #1 startup podcast, with 600K subscribers.
It's Shark Tank without the theater. You hear the actual questions investors ask, the moments a pitch falls apart, and the follow-up episodes where you find out if the deal closed.
Even if you never plan to raise (I'd argue most of you shouldn't), hearing 50 pitches will sharpen how you talk about your own product. Your landing page is a pitch. Your demo call is a pitch.
8. Startups for the Rest of Us
Rob Walling's show, running since 2010. The original podcast for bootstrapped SaaS founders.
Rob built and sold Drip, then started TinySeed (an accelerator for bootstrappers) and MicroConf. When he answers a listener question about pricing or churn, it comes from 15 years of pattern-matching across hundreds of SaaS companies.
It's the opposite of 20VC in the best way. Rob talks to people building profitable software companies without funding, and the advice stays calm and specific even when the topic is scary (like the episode on deciding when to sell).
The real lesson from 20VC (steal this)
Before you go, one thing worth sitting with.
Harry Stebbings didn't start with a fund. He started with a free podcast, recorded between classes, begging VCs for 20 minutes of their time.
The podcast built the network. The network built the brand. The brand raised $140M, then $400M.
The product came after the distribution. Years after.
Most founders do it backwards. They spend 6 months building, then wonder why launch day is silent.
You don't need 1,400 episodes to copy this. You need one channel where you show up every week and talk to people one level ahead of you.
For me that channel is the podcast. Every episode I record, I get a free hour with a founder doing numbers I want to hit. Some of them became friends. A few became members of my mastermind.
That's the actual 20VC playbook, and it costs $0 to run:
→ Pick the people you want to learn from.
→ Give them a stage instead of asking for a favor.
→ Publish everything, consistently, for years.
Harry did it with VCs. I'm doing it with bootstrapped founders. You can do it in whatever niche you sell to.
How to pick (so you don't subscribe to all 8 and listen to none)
Here's the honest filter:
→ Want real numbers from bootstrapped founders? Profitable Founder Podcast or Startups for the Rest of Us.
→ Want business ideas and energy? My First Million.
→ Want to fix your product? Lenny's Podcast.
→ Want investor brains? Invest Like the Best or This Week in Startups.
→ Want stories? Acquired or The Pitch.
Pick two. Listen on 1.5x while you do the dishes. Unsubscribe from anything you skip three times in a row.
And if you want help choosing based on your stage, I ranked the best podcasts for SaaS founders by MRR stage in a separate post.
FAQ
What podcast is most similar to 20VC?
Invest Like the Best is the closest match. Same long-form investor interview format, same caliber of guests, same focus on how great investors think. If you specifically love Harry Stebbings' startup news and hot takes, This Week in Startups scratches that itch better.
Is 20VC worth listening to as a bootstrapped founder?
Sometimes. The founder episodes (like the Monday.com and Synthesia interviews) are genuinely useful at any stage. The fund strategy and LP episodes are not, unless you're raising or just curious. My rule: scan the guest list, skip anything with "fund" in the title.
How often does 20VC publish episodes?
Multiple episodes most weeks, alternating between investor interviews, founder interviews, and news roundtables. The back catalog is around 1,400 episodes, so nobody is catching up from episode one. Start with the guests you recognize.
What's the best podcast for bootstrapped SaaS founders specifically?
Startups for the Rest of Us for fundamentals, and Profitable Founder Podcast for current, numbers-first interviews with founders between $100K and $10M a year. Between those two you cover both the evergreen playbook and what's working right now.
One last thing
Podcasts are input. Your business grows on output.
I capped my own listening at 3 shows because I kept using "learning" as procrastination. (Felt productive. Wasn't.)
So pick your shows, then get back to shipping.
And if you want the bootstrapped version of 20VC, with founders sharing the real numbers behind $100K to $10M a year businesses, start here:
