David Hoffman co-founded Bankless, a media company built on the idea that you can hold and move money without ever touching a bank. He discovered crypto, and things escalated from there.

In this episode, David tries to explain to Henrick what "bankless" actually means, and Henrick spends most of the conversation convinced this means keeping cash in a mattress or a satchel. David explains that his hardware got so hot and loud mining ethereum he had to move it into his father's bathroom. He also reveals that he sold all of his Ethereum, but for how much?

Henrick presses David on banks, blockchains, coins on the sidewalk, capital gains tax, and proposes that AI agents should get a regulated forty hour work week.

David explains: ■ Why he calls a blockchain a ledger ■ How mining Ethereum started in his bedroom and ended in a bathroom ■ Why he sold all of his Ethereum ■ Whether selling below the peak counts as a mistake ■ How capital gains tax applies once crypto becomes "government dollars" ■ Why Henrick thinks AI agents deserve an eight hour work day

This conversation covers Bankless, Ethereum, crypto mining, blockchain, capital gains tax, decentralization, AI agents, regulation, and what happens when a venture capitalist tries to understand crypto for the first time.

——

About Comp AI

Comp AI helps companies build real compliance programs for SOC 2, ISO 27001, GDPR, HIPAA, and more using AI-driven automation.

We focus on continuous compliance, audit readiness, and defensible infrastructure, without spreadsheets, chaos, or manual work.

Austin Nasso worked at Microsoft, studied computer science at UCLA, and then decided to become a stand-up comedian.

In this episode, Austin talks about leaving Microsoft, getting into comedy, and performing political impressions on tour. He also shows off his impressions of Donald Trump, George W. Bush, and Barack Obama, while Henrick quickly gets roasted.

Henrick asks Austin on his background in tech and comedy. See what happens when a stand-up comedian is given a venture capitalist as a target.

Austin explains:

■ Why Austin left Microsoft after four years

■ How studying computer science at UCLA shaped his career

■ Why his friends pushed him into stand-up comedy

■ How he developed his political impressions

■ What it's like performing impressions of presidents

■ Why he went on tour as a stand-up comedian

■ The story behind one of his shows and a very familiar audience member

■ Why Henrick is also, somehow, “succulent”

■ What happens when Henrick becomes the subject of the comedy

——

About Comp AI

Comp AI helps companies build real compliance programs for SOC 2, ISO 27001, GDPR, HIPAA, and more using AI-driven automation.

We focus on continuous compliance, audit readiness, and defensible infrastructure, without spreadsheets, chaos, or manual work.

Ankur Nagpal is the founder of Teachable, the online education platform acquired in 2020, and the founder behind several companies focused on expanding access to entrepreneurship, financial education, and private market investing.

In this episode, Ankur explains how building Facebook apps in college led him into entrepreneurship, why he created Teachable to help creators own their audiences, and what he learned from selling a company during one of the biggest stock market crashes in financial history. He also shares how discovering little-known sections of the U.S. tax code completely changed his understanding of wealth creation and why many founders unknowingly leave millions of dollars on the table.

This conversation covers entrepreneurship, Teachable, startup investing, venture capital, private markets, accredited investor laws, tax code strategy, QSBS, Silicon Valley, financial education, founders, AI startups, compliance, and why access—not ability—may be the biggest barrier to building wealth.