/
© 2026 RiffOn. All rights reserved.

Get your free personalized podcast brief

We scan new podcasts and send you the top 5 insights daily.

  1. Origins: Inside Venture Capital
  2. Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder
Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder

Origins: Inside Venture Capital · Aug 20, 2026

DoNotPay founder Josh Browder on bootstrapping, profitability, and his unique, founder-first investing model at Browder Capital.

DoNotPay Founder's "Ask Forgiveness" Ethos Began with a Cease-and-Desist from Pret-a-Manger

At 14, Josh Browder built an unofficial Pret-a-Manger app. Instead of suing him after sending a cease-and-desist, the company discovered his age and made his creation their official app. This taught him that bold, unsanctioned action can be the most effective path forward.

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder thumbnail

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder

Origins: Inside Venture Capital·2 months ago

Marc Andreessen Convinced DoNotPay's Founder That For-Profit Models Drive Greater Impact Than Non-Profits

Josh Browder initially planned for DoNotPay to be a non-profit. However, a breakfast with Marc Andreessen convinced him that the incentive structures of a for-profit company are more effective for achieving large-scale, mission-driven goals.

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder thumbnail

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder

Origins: Inside Venture Capital·2 months ago

DoNotPay's Founder Pitched a16z's Entire 20-Person Partnership for a $1M Check; Now a Scout Can Write It

Josh Browder highlights the dramatic drop in fundraising difficulty. His $1M pre-seed from a16z required pitching the entire partnership, including its most famous partners. This hurdle is almost unimaginable today, where a single scout can often write a similar check.

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder thumbnail

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder

Origins: Inside Venture Capital·2 months ago

Solo GP Josh Browder's Investment Model Involves Moving One Founder at a Time Into His Spare Bedroom

Browder Capital employs a unique, high-depth investment model. Browder works with only one "pre-pre-seed" founder at a time, moving them into his home and using his entire network to help them get to an institutional seed round before moving on to the next.

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder thumbnail

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder

Origins: Inside Venture Capital·2 months ago

DoNotPay Generated Millions in Revenue by Applying SEO Tactics Learned From a Portfolio Company

A key benefit of being an operator-investor is cross-portfolio learning. Browder learned advanced SEO and organic acquisition strategies from one of his first investments (owner.com) and directly implemented them at DoNotPay, leading to tens of millions in new revenue.

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder thumbnail

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder

Origins: Inside Venture Capital·2 months ago

Investor Josh Browder Never Suggests Product Ideas, Believing It Dilutes Founder Grit

Browder's biggest investing mistake was suggesting what founders should build. Now, he has a strict policy against it. He believes ideas must originate from the founder's own obsession, as this is a core indicator of the grit required for success, and an external idea can discount that.

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder thumbnail

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder

Origins: Inside Venture Capital·2 months ago

LA Parking Bureau Praised DoNotPay for Making Ticket Appeals Easier to Process

Counterintuitively, the head of the Los Angeles parking ticket bureau publicly stated they liked DoNotPay. The service standardized the chaotic process of citizen appeals, making them legible and easier to process, which inadvertently created value for the government agency.

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder thumbnail

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder

Origins: Inside Venture Capital·2 months ago

Investor Josh Browder Vets Founders by Demanding to See Their Stripe Dashboard in the First Meeting

To quickly gauge a founder's honesty and preparedness, Browder employs an "instant validation" technique. If a founder claims to have revenue, he asks them to pull up their Stripe dashboard on their phone right then and there. Any hesitation is a major red flag.

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder thumbnail

Ask Forgiveness, Not Permission: Josh Browder on Building DoNotPay and Investing Like a Founder

Origins: Inside Venture Capital·2 months ago