
Playing With Unicorns
Playing with unicorns is a new weekly show on startups, entrepreneurship, and venture capital.
I cover everything I learned as an entrepreneur, angel investor and venture capitalist during the last 22 years, focusing on everything I wished I knew when I first got started as a tech entrepreneur.
Latest episodes

Jun 20, 2025 • 48min
#50 Venture Market Trends
The venture market is in flux. AI is booming while the rest of venture is in the dumps. Venture capital as an asset class is evolving and retrenching. Fewer deals are happening at higher prices. New marketplace types are emerging. AI is impacting marketplaces in unexpected ways and new technologies are coming of age. There is much to discuss! You can follow along live on LinkedIn, Facebook, YouTube, Twitter, and Twitch. If you are interested in seeing past episodes, including the supporting materials presented during the stream, check out my blog's Playing with Unicorns section. It takes me a while to write episode summaries. For the latest shows, check out Playing With Unicorns on YouTube, Spotify, or iTunes.

Jun 9, 2025 • 52min
#49 Dan Park and the Incredible Comeback Story of Clutch
Clutch has had an incredible ride. As the “Carvana of Canada” it was a highflier in 2021. It had a brush with death in 2023 and effected an incredible turnaround. They are now once again on a tear. Dan Park, Clutch’s Founder & CEO, joined us to share all the lessons learned along the way.

Apr 22, 2025 • 1h 48min
#48 Ask Me Anything
There’s a deep dive into how geopolitical changes are shaping global trade and tech investments. Tips for persuading investors and the future of fashion marketplaces highlight the conversation. The speaker shares innovative wealth management strategies ideal for entrepreneurs. Excitingly, they discuss the potential impact of AI and humanoid robots in our daily lives. Personal stories, like a snow kiting adventure turned injury, provide insights on resilience and startup challenges, while addressing education for the jobs of the future.

Dec 16, 2024 • 56min
#47 Marketplace Trends
Discover the exhilarating future of marketplaces! Dive into cross-border commerce and the rise of live video sales. Learn about innovative niche marketplaces, from restaurant equipment to children's books. Explore the impact of climate tech on energy solutions and how automation is reshaping installations. Uncover the transformation in B2B platforms, driven by user-centric models and AI. Plus, get insights into real estate trends, AI's influence on customer experiences, and the challenges of market fluctuations!

4 snips
Nov 18, 2024 • 1h 14min
#46 FJ Labs’ AI Thesis
The discussion revolves around AI's booming influence in venture capital, contrasting the current investment landscape. Insights into AI's disruptive potential across various sectors, including sports, fashion, and healthcare, are shared. The conversation highlights the transformative effects of AI on job roles without complete replacement. Strategic advice for entrepreneurs exploring AI solutions is provided, alongside personal anecdotes about marketplace success. Additionally, thrilling plans for extreme adventures add a fun twist to the insightful journey.

Apr 10, 2024 • 1h 51min
#45 Ask Me Anything
Topics covered in this podcast include AI trends, augmented reality, starting OLX, Midas details, retail investor opportunities, seed round insights, crypto market perspectives, activism in startups, potential fiat currency crisis, future adventure plans, marketplace validation, AI investments, and job evolution amidst technological advancements.

18 snips
Jan 11, 2024 • 1h 12min
#44 Unlocking Productivity: Streamlining Your Days for Passion and Purpose
In this podcast, the speaker shares secrets to accomplish a lot in a passionate life. They discuss outsourcing tasks, minimizing news consumption, managing business and personal life, creating a yearly photo album, acknowledging financial privilege, imposter syndrome and happiness, and the effectiveness of virtual assistants.

Sep 10, 2023 • 1h 15min
#43 Julio Vasconcellos and the state of Latin American tech
I had the pleasure of receiving Julio Vasconcellos on the show. Julio is the Founder and Managing Partner of Atlantico, a leading early-stage venture fund in Latin America. It was Julio's role as the inaugural Facebook employee for Latin America that initiated his path in the startup world in the region after starting his career in Silicon Valley. He later co-founded Peixe Urbano, scaling it to over 1,200 employees and $100M+ in revenue. After a startup rollercoaster ride with multiple near-death experiences, Julio sold the company to Baidu, and went on to join Benchmark Capital as an Entrepreneur-in-Residence. There, he met Scott Belsky and the two went on to co-found Prefer in San Francisco which Benchmark backed, as they had with Peixe Urbano. Alongside his entrepreneurial journey, Julio has been investing for over a decade. Starting as a seed investor, he co-founded Graph Ventures with fellow colleagues from Facebook and Stanford. Later, he helped co-found Canary (https://canary.com.br/), the leading seed-stage fund in Latin America. In 2020, Julio returned to Brazil to found Atlantico and focus on early-stage venture investing. We covered: His history and path into tech. His transition from entrepreneur to investor. Why he built Atlantico to focus on Series A investing in Latin America. The significant investment potential within Latin America today.

Mar 17, 2023 • 1h 9min
#42 Kevin Ryan, Unicorn Builder
I had the pleasure of being joined by my good friend Kevin Ryan. He’s often been called the “Godfather of NYC tech.” Kevin is one of the leading internet entrepreneurs and investors in New York. He is a co-founder of MongoDB, Business Insider, Gilt Groupe, Zola, and Nomad Health, and founds new companies with AlleyCorp every year. Earlier in his career, Kevin helped to grow DoubleClick first as President and then as CEO, leading their growth from a 20-person startup to a publicly traded global leader with over 1,500 employees, through IPO in 1998 and acquisition by Google in 2007. Kevin is also on the Board of Tech:NYC, Vice Chairman of The Partnership for New York City, a member of the CFR Committee on Foreign Affairs, and Director Emeritus for Human Rights Watch. Kevin previously served on the boards of the Yale Corporation and INSEAD. It's also worth mentioning Kevin is the one who convinced me to go to Antarctica with him. We covered: · His history and path into tech. · How he built so many successful companies with Alley Corp. · Lessons learned along the way. · His general life philosophy and perspective on Antarctica, Burning Man, psychedelics and much more.

Feb 12, 2023 • 1h 53min
Episode 41: Ask Me Anything
It had been over a year since we did the last Ask Me Anything (AMA) so the time had come. As requested by the audience, my son François joined us for the first part of the show. He was his usual epic self: calm, poised, and playing along cutely. His presence clearly played a part in the success of the episode which was one of the most watched ever across all the platforms and was by far the most interactive episode ever with 137 live comments in addition to dozens of questions submitted ahead of time! The audience’s questions fell into 5 categories: Antarctica, Marketplaces, Startups, Macro, and Other (life decisions, books, etc.) which I covered in turn.