This week, we’re taking a look back at some of my favorite moments from the past year—the conversations that stuck with me long after we hit stop on the recording. If you missed them the first time around, now’s your chance to catch the highlights!

And here’s the kicker—every one of the eight segments I pulled together features 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 linkto register here.

LINKS:

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

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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 Pinscmidt

• 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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Alejandro Gutierrez joins me once again to dive into some of the biggest conversations in crypto right now, including:

• The fallout from Operation Chokepoint 2.0 and the debanking of crypto startups—what it means for the industry and how regulatory shifts in the U.S. and Europe could reshape the future of digital assets.

• Why Solana is having its moment—how Solana's DEX volume is outpacing Ethereum’s and what this means for the long-term viability of the network.

• The rise of decentralized exchanges (DEXs) and why Uniswap launching its own Layer 2, Unichain, could be a game changer.

• Institutionalization of crypto—how Solana ETFs and BitGo’s rumored IPO are bringing more traditional finance players into the space.

• The evolving regulatory landscape—what the SEC’s new stance on crypto, led by Commissioner Hester Peirce, could mean for the industry’s future.

Plus, we share the details on an exciting new event—Techstars and CryptoMondays Ireland are teaming up for a first-of-its-kind gathering in Dublin on March 10th (register here).

Alejandro Gutierrez is a leading figure in the decentralized finance (DeFi) space and an early adopter of real-world asset tokenization. Alejandro has contributed to the growth of DeFi through his work with MakerDAO, Tokeny, Securitize, and Centrifuge, as well as his co-founding of Consolfreight, Defactor, and ETH Dublin.EPISODE LINKS:

Operation Chokepoint 2.0 / Debanking

Coinbase - the facts are the facts FDIC (X, 6-Feb-25)

Operation Chokepoint 2.0 - Nic Carter, Castle Island Ventures (Pirate Wires, 8-Feb-23) 

Marc Andreessen on Joe Rogan (Joe Rogan Experience, 27-Nov-24)

Fed's Powell Says He's Also Worried About Debanking (Coindesk, 11-Feb-25)

Graham Rodford from Archax on the UK situation (Linkedin, recently)

New Era in the SEC with Crypto

The Journey Begins - SEC Commissioner Hester Peirce (SEC, 4-Feb-25)

Other Topics

Solana DEX Volume Tops $60M as It Looks to Extend 4-Month Winning Streak Over Ethereum (Coindesk, 11-Feb-25)

BitGo Mulling IPO This Year (Coindesk, 11-Feb-25)

Uniswap Labs Officially Launches Layer-2 ‘Unichain’ (Coindesk, 10-Feb-25)

Keywords:  #OperationChokepoint2 #debanking #SolanaDEXvolume #UniswapLayer2 #Cryptoregulation2025 #DeFI #Institutionalcryptoadoption #SolanaETFs #seccryptopolicy

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This week, we’re tapping into the intersection of hip-hop, technology, education and startups with a true pioneer—Arabian Prince.

If you know your rap history, you know Arabian Prince as one of the founding members of N.W.A, the Rock and Roll Hall of Fame rap group that redefined music and culture. But what you might not know is that he’s also a lifelong technologist, entrepreneur and futurist—a kid from Compton who got his hands on a computer early and never looked back.

From songwriting, rapping and DJ-ing to producing electro-funk beats and Grammy-nominated #1 hit song Supersonic to leading innovation in 3D animation, video games, and blockchain, he’s been pushing the boundaries of technology for decades.

In this episode, we talk about how a chance encounter with an N.W.A-inspired crypto-merch baseball cap led to this conversation, and from there, we cover everything—his early love for tech, how music and technology shaped his career, and his mission as founder of INov8 Next Open Labs and co-founder of INov8 Capital to bring the next generation of kids into the world of tech.

Form beats to bytes, Arabian’s story is all about curiosity, hustle, creativity, and breaking boundaries—whether it’s in music, business, or technology, so this is one you don’t want to miss.

EPISODE LINKS

QUOTES FROM THE EPISODE

SHOW NOTES 

01:45 – The backstory: A crypto merch cap leads to this conversation

04:10 – Growing up in Compton, discovering computers, and early influences

08:50 – Blending music and technology: from electro-funk to hip-hop

11:15 – The birth of N.W.A and leveraging tech in the studio

14:40 – Why Arabian Prince left N.W.A and pivoted into animation and video games

16:20 – Working on Mighty Morphin Power Rangers, Silver Surfer, and Casper

18:30 – Founding iNov8 Next Open Labs and building tech education initiatives

21:05 – The regional approach: Adapting tech education to different U.S. communities

24:15 – Leveraging relationships and hip-hop’s legacy to open doors in tech

27:40 – Thoughts on blockchain, AI, and the future of digital ownership

29:50 – The impact of teaching kids about technology and entrepreneurship

32:00 – Fun facts about Arabian Prince: his love for SpongeBob and video games

34:00 – Arabian’s connection to Ireland and plans for visiting soon

35:00 – Closing thoughts and where to find Arabian Prince online

Keywords:

Shout-outs and hat-tips: Amor Sexton, Philipp Pieper, Timo Lehes, Katie Evans, Kene Ezeji-Okoye

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Laura Walsh returns this week to help me unpack the whirlwind of events shaking up crypto, finance, and politics—from Trump’s memecoin antics to regulatory shifts and the ever-increasing adoption of crypto by institutional finance.

Laura Walsh is a Techstars All Star Mentor, advisor, founder, web3 OG and friend, and in this episode, we dive into:

There’s no shortage of action in this episode—memecoins, market shifts, regulatory updates, and some fascinating history lessons all packed into one conversation!

Gary Gensler Leaves SEC, and Cryptocurrency-Friendly Mark Uyeda Is Appointed (Binance, 20-Jan-25)

SEC Forms New Crypto Task Force Spearheaded by Hester Peirce (CoinDesk, 21-Jan-25)

Trump’s meme coin is a reminder of crypto’s dumbest use case (CNN, 21-Jan-25)

Alternative viewpoint on memecoins from Kevin DeGods (X/Twitter, 20-Jan-25)

Canada has threatened ‘dollar for dollar’ retaliatory tariffs and ‘nothing is off the table’ (National Post, 21-Jan-25)

The Irish whiskey playbook: an insider’s guide to how firms must navigate Trump’s DC (Business Post, 20-Jan-25)

Dfns Raises $16 Million to Expand Crypto Wallet Infrastructure (Pymnts.com, 17-Jan-25)

Circle buys tokenized money market fund Hashnote-USYC (Finextra, 21-Jan-25)

Tornado Cash off OFAC List (Cointelegraph, 22-Jan-25)

Ross Ulbricht pardoned (X, 21-Jan-25)

Connect with Laura Walsh on social media:

Linkedin: https://www.linkedin.com/in/lauralwalsh/

Twitter: https://twitter.com/TheOGLauraWalsh

Keywords: Trump, memecoins, crypto, regulations, SEC, tokenized assets

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Brian McDonald is a partner at Bay Advisory, a corporate finance firm helping founders navigate funding, scaling, and exiting their businesses. Brian first joined the show in 2021, and now, four years later, he returns to share updated insights on startup exits, valuations, and the evolving market landscape.

From the importance of staying true to your business identity to understanding deal structuring and negotiation tactics, Brian breaks down what founders need to know before, during, and after an exit. He also shares his thoughts on current trends, including valuation shifts, the rise of AI-driven businesses, and the significance of knowing when to walk away from a deal.

If you’re a founder planning your next fundraising round or thinking about an exit, this episode is packed with actionable advice and real-world examples that you won’t want to miss.

Key Takeaways

1. Stay True to Your Business Identity:

Many founders feel pressured to present their business as a SaaS or AI-driven venture to attract investors, but Brian emphasizes the importance of positioning your business based on what it truly is rather than shaping it to fit investor expectations.

2. Avoid Venture Capital If You Plan to Keep Your Business Long-Term:

If you’re building a business to own and operate for life, taking on investors expecting a return may not be the right move. Transparency about your vision is crucial in aligning with the right partners.

3. Consider Alternatives to Full Exits:

Founders don’t have to sell their entire company to achieve financial security. Partial exits or taking some cash off the table while continuing to scale can be viable options.

4. Valuation Challenges in Today’s Market:

Valuations fluctuate, and generic revenue multiples can be misleading. Founders should focus on comparable deals and be realistic about their company’s value in the current market conditions.

5. Earnouts and Deal Structuring:

Few exits involve a full cash payout at closing. Earnouts based on future performance are common, and founders should aim for turnover-based earnouts rather than EBITDA-based, as buyers can manipulate EBITDA figures..

6. Know Your ‘No’ and Be Ready to Walk Away: Understanding your bottom line in negotiations is critical. If a deal isn’t right, having the confidence to walk away can save founders from making costly mistakes.

Longer Deal Timelines: Exit processes that once took six months are now stretching to 9-12 months due to market shifts.

AI Bubble: Many businesses are branding themselves as AI-driven when they’re not, which mirrors past trends seen with blockchain startups.

Corporate vs. PE Buyers: Corporates focus on strategic fit, while PE firms prioritize financials and growth potential.

Importance of Data Rooms: Keeping updated documentation can streamline fundraising or an acquisition process when the time comes.

Guest Details:

Email: [email protected]

Website: BayAdvisory.ie

LinkedIn: Brian McDonald

Listen to Brian’s first appearance on MoneyNeverSleeps in 2021 (episodes 118 and 119, Words of Advice, Parts 1 &2)

Learn more about Bay Advisory and their advisory services for founders

Brian referred to the book A Slight Edge by Jeff Olson in focusing on your niche at the earliest stages

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In this special year-end episode, Pete Townsend is joined by returning guest co-host Alejandro Gutierrez for a wide-ranging conversation about what the future may hold in 2025. Together, they explore transformative ideas, emerging trends, and groundbreaking technologies that could shape industries, disrupt norms, and redefine global innovation. From traditional finance’s embrace of tokenization to the rise of AI agents, the duo covers it all—including a bonus prediction from a mysterious contributor. Tune in for an exciting glimpse into 2025 and get ready to peer into the crystal ball with Pete and Alejandro.

What You’ll Learn:

Bonus Predictions: Eoin Motherway, fintech and funds industry legend, shared his take on 2025:

Resources Mentioned:

Call to Action: If this episode sparked your curiosity about 2025, we’d love to hear your predictions! Share your thoughts on X/(Twitter) at @MNSShow or email us at [email protected]. Don’t forget to subscribe, rate, and review MoneyNeverSleeps on Apple Podcasts and Spotify—and share this episode with a friend.

Keywords: Alejandro Gutierrez, Pete Townsend, 2025 tech trends, Blockchain and AI, Crypto trends 2025, Stablecoins future, Decentralized identity solutions, Bitcoin mining expansion, Tokenization in finance, web3 trends 2025

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This week, I interviewed serial entrepreneur Nigel Eccles. Known for his role as co-founder and former CEO of FanDuel, Nigel shares his incredible journey of launching and scaling multiple ventures, including his latest projects BetHog and BetDex. Nigel dives into the pivotal moments that defined his career, lessons learned from raising over $450 million in venture funding, and his insights into the evolving landscapes of crypto, Web3, and gaming.

Nigel’s candid reflections on timing, co-founder dynamics, and building resilient startups are a must-hear for founders, investors, and anyone curious about how to stay ahead in the world of tech and entrepreneurship.

What You’ll Learn in This Episode:

Notable Quotes:

Connect with Nigel Eccles: Twitter | LinkedIn

Keywords: gaming, sports betting, FanDuel, crypto, web3, BetHog, BetDex, fundraising, venture capital

Shout-outs: Connor Murphy, Bradley Tusk, Nic Carter

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This week, I’m joined by the brilliant Mai Santamaria for a far-ranging discussion inspired by Ian Goldin’s concept of The Butterfly Defect — a thought-provoking take on the risks and interconnectedness of our global systems. We dive into how this idea resonates with the evolution of crypto, web3, and the financial markets, and explore how the convergence of traditional and decentralized systems could reshape the future.

Mai, an award-winning fintech and financial policy expert, has been a trailblazer in shaping regulatory and strategic frameworks in Ireland. With deep expertise in digital finance and a passion for innovation, Mai brings her unique perspective to our conversation, exploring the challenges—and opportunities—of hyper-connectivity in our global economy.

It's a deep and engaging conversation that offers insights into how globalization, technology, and finance intertwine

IN THIS EPISODE:

- The Butterfly Defect: How hyperconnectivity increases systemic risks and the lessons for crypto and globalization.

- Parallel Arcs of Financial Systems: The inevitable convergence of traditional financial markets and crypto.

- Regulatory Perspectives: Why interconnectedness demands careful collaboration at a global level.

- The Role of Technology: How blockchain innovation like self-executing smart contracts can reshape financial markets.

- Echo Chambers: Navigating the challenges of being too immersed in niche ecosystems and staying grounded.

- Ireland’s Potential: How Ireland’s geographical and technological advantages position it as a hub for sustainable digital financial services.

- Emerging Market Innovation: The surprising use cases for stablecoins and tokenized assets in emerging markets.

KEYWORDS:

butterfly defect, globalization, digital economy, crypto, blockchain, web3, regulation, stablecoins, butterfly effect

RESOURCES:

Follow our guest co-host Mai Santamaria on LinkedIn: https://www.linkedin.com/in/mai07/

The Fintech 15: Meet the Women Shaping the Irish Revolution (paywall)

The Fintech Blueprint podcast interview with Tom Duff Gordon from Coinbase

Professor Ian Goldin’s 2014 Princeton lecture on The Butterfly Defect

Meet Keith Gill, the man who drove the GameStop Reddit mania and made millions

Aled Jones’s article The Actuary (2021) on the Butterfly Defect

The Stablecoin Revolution with Linda Jeng | Unpacking Castle Island Ventures’ Latest Stablecoin Report

David Senra’s Founders podcast

LINKS:

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This week. I sat down with Timo Lehes and Philipp Pieper, the co-founders of Swarm, the RWA (or Real World Assets) platform that brings unique digitization and trading solutions to the world of traditional and decentralized finance. Swam is the first organization in the world to offer digitized US treasury bills and Apple stock via a compliant and decentralized platform

From their personal journeys into crypto to the challenges of integrating TradFi with DeFi, Timo and Philipp unpack Swarm's evolution, their focus on compliance, and their vision for the tokenized financial markets of tomorrow. Along the way, they share stories about formative moments in their careers, including Philipp’s time in New England during the fall of the Berlin Wall and Timo’s early coding days.

Plus, we dive into:

Key Takeaways:

About Swarm: Swarm is a compliance-first platform for tokenizing real-world assets, combining the speed, efficiency, and flexibility of blockchain with the trust and asset diversity of traditional exchanges. By integrating TradFi with DeFi, Swarm aims to create a seamless future where everything just becomes “Fi.”

Follow Swarm:

Connect with Timo and Philipp:

Mentioned in This Episode:

Keywords: crypto, blockchain, digital assets, tokenization, real world assets, RWAs, DeFi  

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This week, we’ve got an exclusive interview with Manu, the founder and CEO of Sponstar, the fractional sponsorship marketplace that’s leveling the playing field for small and mid-sized brands to access high-profile sponsorship opportunities. Manu’s entrepreneurial journey, from traditional finance to web3, led to the creation of Sponstar—a game-changing platform that bridges physical events and digital experiences while redefining the sponsorship ecosystem.

Manu shares her insights on fractional sponsorship, the intersection of blockchain, AI, and event marketing, and the unique challenges women founders face in the tech and crypto worlds. We also explore her guiding principles of spirituality, surrender, and how giving more strengthens a startup’s potential.

Manu previously co-founded Alpha’a and alphaa.io where she changed the way companies connect with their fans, using web3 to help enterprises connect people, content and experiences.  She has been in the tech and collectibles sector for the past 10 years successfully raising funds from venture investors such as Metaprop, Lightspeed, Chingona Ventures, and Gaingels  With a background in finance, Manu worked as an equity analyst at Gávea Investments, one of Brazil’s most reputable investment management firms.

Notably, Manu was named by Bloomberg in 2022 as one of the top 100 most influential Latinos and Latinas worldwide, one of the top 10 people to watch in Fintech in 2023, and one of the 33-Under-33 entrepreneurs in 2018 in New York City. 

RESOURCES & LINKS:

Learn more about ⁠Sponstar⁠

Recommended Reading: ⁠The Surrender Experiment by Michael Singer⁠

ABOUT THE HOST:

Pete Townsend is an early-stage startup investor focused on the intersection of fintech, crypto, and web3. He also leads the ⁠Techstars Web3 Accelerator⁠. For more on Pete and how to get in touch, visit ⁠moneyneversleeps.ie⁠.

SUPPORT THE SHOW:

If you enjoyed this episode, please leave us a review on ⁠Apple Podcasts⁠ or ⁠Spotify⁠, and don’t forget to subscribe for future episodes of MoneyNeverSleeps. Until next time, stay curious and keep learning!

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