285: Startup Smarts & Web3 Wisdom | Highlights from the Past Year

And here’s the kicker—seven of the eight segments I pulled together feature a mentor from the Techstars Web3 Accelerator that I lead. It’s part highlight reel, part "thank you" to these incredible people who help founders navigate the startup grind. A huge shoutout to Mai Santamaria, Patrick Pinschmidt, Hesus Inoma, Rita Martins, Alejandro Gutierrez, Laura Walsh, Philipp Pieper, Timo Lehes, and Arabian Prince from NWA for sharing their wisdom.

A number of these guests will also be joining us at the Techstars x Crypto Mondays Ireland event that Hugh McGirr and I are hosting in Dublin on Monday, March 10th at Toner’s Pub. If you’re around, come reconnect with old friends, meet new builders, investors, and operators across Web2, Web3, and enterprise, and hear from our Techstars Web3 Class of 2025. You might even enjoy a pint of Guinness while you’re at it. Check out the Luma link to register here.

EPISODE HIGHLIGHTS:

Mai Santamaria on AI, Vitalik Buterin’s Manifesto, and the Role of Technology (ep 241)

One of the most thought-provoking conversations of 2023 was with Mai Santamaria. We riffed on Vitalik Buterin’s manifesto, the societal role of AI, and how the way we train AI today will shape its long-term impact. Mai compared AI to a child learning from the world around it—if we feed it negativity, that’s what it will learn. Deep stuff!

Patrick Pinschmidt on the Investor Mindset and the Power of Lines, Not Dots (ep 248)

Patrick Pinschmidt from MiddleGame Ventures joined me to talk about deal flow in venture capital. One of my biggest lessons learned after looking at over 2,000 Techstars deals? Investors invest in lines, not dots. It’s all about building relationships over time, understanding how founders execute, and ensuring alignment before the first check is written.

Hesus Inoma on the Core Traits of Great Founders (ep 257)

In my episode with Hesus Inoma, we went deep on what makes a great founder. The key traits? Honesty, focus, ambition, and resilience. Also, if your LinkedIn says you’re running five startups at once—huge red flag. Founders who execute relentlessly and listen to feedback are the ones who make it.

Rita Martins on the Convergence of TradFi and Web3 (ep 264)

With Rita Martins, we talked about the ongoing collision of traditional finance (TradFi) and Web3. It’s happening faster than people think, and big financial players are moving into tokenization and digital assets. The worlds of DeFi and TradFi are converging, and if you’re in finance and not paying attention, you’re at risk of being disrupted.  Check out Rita’s book Web3 in Financial Services here..  

Alejandro Gutierrez on the Rise of Stablecoins and What Comes Next (ep 269)

Alejandro Gutierrez and I got fired up about stablecoins as the killer app for crypto. The big shift? Countries like Brazil and Mexico now have native access to USDC, which changes everything for cross-border payments and financial inclusion. The real question: what happens when interest rates drop? The yield-driven stablecoin boom will need a new playbook.

Laura Walsh on Why We Don’t Need a U.S. CBDC (ep 266)

My conversation with Laura Walsh was a fiery one. We both agreed that a U.S. central bank digital currency (CBDC) is a bad idea. Why? Privacy concerns, potential government overreach, and the fact that stablecoins already do the job better. Plus, banks already have enough control over financial access—a programmable dollar would only tighten their grip.

Philipp Pieper & Timo Lehes on RWA, the Swarm Origin Story, and That Iconic Hat (ep 277)

Philipp Pieper and Timo Lehes from Swarm joined me to talk about the real-world asset (RWA) revolution and how tokenization is unlocking new opportunities. Also, shoutout to Katie Evans from Swarm for creating the iconic RWA hat, styled after NWA’s logo. Who knew that nostalgic counterculture crypto merch would turn into such a phenomenon?

Arabian Prince on Tech, Music, and Building Through Relationships (ep 283)

Rounding out this highlight reel, I had the privilege of interviewing Arabian Prince from NWA. The legendary artist-turned-entrepreneur talked about leveraging relationships to build the future, why he stays at the cutting edge of technology, and how his network has helped him shape new innovations.

LINKS:

Keywords: #techstars #mentors #web3 #cbdc #beststartupinsights #entrepreneurship #podcast #startupecosystem #venturecapitalinsights #blockchaintrends #AI #crypto #fintechinnovations

Check out all of the original episodes we featured:

• 241: Money Talks with Mai Santamaria | Binance and CZ | Argentina's New President | Vitalik's Techno-Optimism Manifesto | Blockchain and AI Intersect

• 248: Venture Investing and Connecting the Dots with Patrick Pinschmidt

• 257: How I Got To Techstars on a Flywheel | Hesus Inoma Interviews Pete Townsend | Venture With Hesus

• 264: Rita Martins | Author of Web3 in Financial Services

• 269: Working in Web3 | Real World Asset Tokenization in Finance and Beyond | Guest Co-Host Alejandro Gutierrez

• 266: Crypto Politics: Unpacking Trump's Campaign Promises with Laura Walsh

• 277: Straight Outta Crypton | Swarm and the Rise of RWAs | Timo Lehes and Philipp Pieper

• 283: Arabian Prince | The N.W.A Pioneer Empowering the Next Tech Generation

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