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281: The Art of Startup Exits | Brian McDonald from Bay Advisory
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. Market Trends and Strategic Insights: 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 Leave a review and subscribe on Apple Podcasts Spotify MoneyNeverSleeps (website) Email us: [email protected] Follow on X(Twitter): Pete Townsend: https://twitter.com/petetownsendnv MoneyNeverSleeps: https://twitter.com/MNSshow Follow on LinkedIn: Pete Townsend: https://www.linkedin.com/in/pete-townsend-1b18301a/ MoneyNeverSleeps: https://www.linkedin.com/company/28661903/ MoneyNeverSleeps newsletter: https://moneyneversleeps.substack.com/
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280: 2025 Predictions with Alejandro Gutierrez
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: Tokenization Takes Center Stage: How traditional finance is poised to fully embrace tokenization, opening up new markets and investment opportunities. Stablecoins in E-commerce: The role of stablecoins in reshaping online payments and the potential for major adoption by e-commerce giants. Decentralized Identity: Why verifiable credentials and self-sovereign identity could become mainstream. Blockchain and Gaming: Predictions for how large gaming studios might integrate blockchain into their IP to empower users with ownership. AI Meets Blockchain: The emergence of AI agents in Web3 and their potential to revolutionize decision-making and commerce. Regulatory Milestones: The Financial Innovation and Technology (FIT21) Act and its potential to establish a clear framework for digital assets in the U.S. Global Bitcoin Adoption: How BRICS nations and others might accelerate Bitcoin mining and adoption for financial sovereignty. Memecoins and AI Agents: The possibility of AI agents driving the next wave of meme coin mania and their implications for the ecosystem. Bonus Predictions: Eoin Motherway, fintech and funds industry legend, shared his take on 2025: Proliferation of Stablecoins: Beyond USD-pegged options, expect growth in other fiat-backed stablecoins (e.g., HKD, JPY). Tokenization of Funds: The tokenization of money market funds could gain momentum, paving the way for more accessible and efficient investments. Digital Assets Ireland: The emergence of Ireland as a hub for digital assets under MiCAR regulations. Resources Mentioned: Electric Capital Developer Report 2024 Castle Island Ventures: Stablecoins and Emerging Markets a16zcrypto: A few of the things we’re excited about in crypto (2025) a16zcrypto’s Chris Dixon on Tetragrammaton with Rick Rubin Bankless Podcast on AI Agents and Finance 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 Leave a review and subscribe on Apple Podcasts Spotify MoneyNeverSleeps (website) Follow our guest co-host Alejandro Gutierrez: X(Twitter): https://twitter.com/A_gutierro LinkedIn: https://www.linkedin.com/in/alejandro-gutierrez-98979b43/ Email us: [email protected] Follow us on X(Twitter): Pete Townsend: https://twitter.com/petetownsendnv MoneyNeverSleeps: https://twitter.com/MNSshow Follow us on LinkedIn: Pete Townsend: https://www.linkedin.com/in/pete-townsend-1b18301a/ MoneyNeverSleeps: https://www.linkedin.com/company/28661903/ MoneyNeverSleeps newsletter: https://moneyneversleeps.substack.com/
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279: Mastering the Startup Game | Nigel Eccles | Insights from a Serial Entrepreneur
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: A speedrun through Nigel’s backstory The early days of FanDuel and lessons from building a billion-dollar business. Insights into raising capital—from seed rounds to $450M in funding. Why timing and market dynamics matter more than ever. The role of ethics and trustworthiness in choosing co-founders and investors. Building for users: Why understanding your audience is key. The future of online gaming, streaming, and crypto’s role in innovation. Notable Quotes: “If you’re a tech startup, you need a tech co-founder. It’s almost impossible to succeed without one.” “The best hires often come from failed startups—they’ve been through the fire and still want to build.” “The key to raising capital is timing and understanding what the market values.” 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 Leave a review and subscribe on Apple Podcasts Spotify MoneyNeverSleeps (website) Email us: [email protected] Follow on X(Twitter): Pete Townsend: https://twitter.com/petetownsendnv MoneyNeverSleeps: https://twitter.com/MNSshow Follow on LinkedIn: Pete Townsend: https://www.linkedin.com/in/pete-townsend-1b18301a/ MoneyNeverSleeps: https://www.linkedin.com/company/28661903/ MoneyNeverSleeps newsletter: https://moneyneversleeps.substack.com/
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278: Money Talks w/ Mai Santamaria | The Butterfly Defect & the Future of Finance
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: Leave a review and subscribe on Apple Podcasts Spotify MoneyNeverSleeps (website) Email us: [email protected] Follow on X(Twitter): Pete Townsend: https://twitter.com/petetownsendnv MoneyNeverSleeps: https://twitter.com/MNSshow Follow on LinkedIn: Pete Townsend: https://www.linkedin.com/in/pete-townsend-1b18301a/ MoneyNeverSleeps: https://www.linkedin.com/company/28661903/ MoneyNeverSleeps newsletter: https://moneyneversleeps.substack.com/
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277: Straight Outta Crypton | Swarm and the Rise of RWAs | Timo Lehes and Philipp Pieper
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: Swarm’s focus on making blockchain-based assets accessible and tradable globally. Insights from the initial coin offering (ICO) and security token offering (STO) waves of the mid-2010s. The importance of regulatory clarity for tokenization to thrive. The role of RWAs in bridging the gap between decentralized and traditional finance. And yes, the story behind Swarm’s iconic RWA baseball caps inspired by 80s rap legends NWA! Key Takeaways: The transition from niche assets to tokenizing well-known RWAs like stocks and gold has been pivotal for Swarm's success. Compliance and regulation are at the heart of Swarm's approach, paving the way for global adoption. Despite the challenges, blockchain holds the potential to simplify and disrupt traditional financial systems, much like the early internet. Swarm's dual focus: Issuing RWAs and providing the tools for others to tokenize assets through their SaaS platform. 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: Website: swarm.com Twitter: @SwarmMarkets Telegram: Swarm Community Connect with Timo and Philipp: Timo Lehes: Twitter | LinkedIn Philipp Pieper: Twitter | LinkedIn Mentioned in This Episode: Dead Poets Society and its influence on Philipp’s philosophy of independent thought. Regulatory developments in the U.S. and Europe, and their implications for tokenized markets. The role of stablecoins as the first real-world asset success story. NWA’s influence on Swarm’s RWA hats—bridging culture and finance. Keywords: crypto, blockchain, digital assets, tokenization, real world assets, RWAs, DeFi Leave a review and subscribe on Apple Podcasts Spotify MoneyNeverSleeps (website) Email us: [email protected] Follow on X(Twitter): Pete Townsend: https://twitter.com/petetownsendnv MoneyNeverSleeps: https://twitter.com/MNSshow Follow on LinkedIn: Pete Townsend: https://www.linkedin.com/in/pete-townsend-1b18301a/ MoneyNeverSleeps: https://www.linkedin.com/company/28661903/ MoneyNeverSleeps newsletter: https://moneyneversleeps.substack.com/
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A weekly podcast that looks inside the minds of entrepreneurs and at the crossover of startups, enterprise, finance, technology and life as we know it, hosted by early-stage startup investor Pete Townsend.

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