Playing With Unicorns

Fabrice Grinda
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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.

  1. 18 HR AGO

    #53 Ask Me Anything

    It's been a year since my last Ask Me Anything session. A lot has happened since then across AI, marketplaces, macro, and the broader tech ecosystem. Here are the questions we covered: ·      4:22 Why does AI feel so widely feared or disliked right now? ·      8:48 Why is AI driving massive progress while politics and public systems lag behind? ·      13:34 What are the real opportunities in commercializing AI today? ·      14:10 Will startups still need human co-founders in an AI-first world? ·      17:51 How important is a technical co-founder in the age of AI? ·      20:00 Will intelligence (IQ) become irrelevant as AI improves? ·      20:18 What skills should young professionals focus on in an AI-driven world? ·      22:48 How should education evolve in the age of AI (and how should kids be taught)? ·      26:40 What drives investor decisions at the earliest stages of a startup? ·      28:23 How can pre-seed founders raise capital, especially outside the US? ·      30:11 How might graph neural networks impact marketplaces? ·      31:32 What does it take to win in marketplaces in regions like Latin America? ·      33:10 What creates real defensibility in AI companies vs hype-driven growth? ·      35:38 Are we in an AI bubble—and what does it mean for investors? ·      37:30 What is the right funding path for startups that require large upfront capital? ·      38:54 What proof do investors need before funding an early-stage startup? ·      39:40 How has your marketplace investment thesis evolved in the age of AI? ·      42:02 Where can founders find strong fractional developers? ·      43:15 What defines AGI—and how should we think about it today? ·      45:08 How important is the initial "wedge" in building a marketplace? ·      46:29 How do you evaluate whether AI adoption actually creates value? ·      48:00 What founder traits matter most today? ·      49:45 If you were starting today, what would you build and why? ·      52:32 Who are you beyond your professional identity? ·      55:11 Do you still have insecurities—and how do you think about them? ·      57:10 What would you do if you weren't an entrepreneur? ·      59:45 What signals show a marketplace is reaching liquidity and product-market fit? ·      1:01:19 What is the core defensibility of a marketplace from day one? ·      1:02:24 What is Quince and why has it been so successful? ·      1:04:22 Which "boring" industries will produce the next big companies? ·      1:06:36 What is the biggest blind spot among VCs today? ·      1:08:15 Which AI sectors are overcrowded right now? ·      1:09:35 Can marketplaces succeed around complex, multi-service life events? ·      1:11:41 How have fundraising expectations changed in the AI era? ·      1:16:07 Should graduates join startups or big companies in 2026? ·      1:16:21 Is being a generalist still a viable career path? ·      1:18:35 Do investors prefer warm intros or cold outreach? ·      1:19:55 Should startups use services as a wedge before becoming SaaS? ·      1:22:02 What games or tools are best for child development and learning? ·      1:24:39 Will AI cause massive job losses or unemployment? ·      1:30:57 Can venture-scale companies be built in Latin America today? ·      1:32:26 How should AI be used in operational decision-making? ·      1:36:00 What separates massive marketplaces from niche ones? ·      1:37:24 How much decision-making should be delegated to AI vs humans? ·      1:39:10 What matters most in early-stage B2C startups: traction or insight?

    1h 40m

  2. 9 MAR

    #52 Marketplaces in the Age of AI

    Over the past few weeks, a growing narrative has emerged arguing that AI could destabilize the economy and disrupt entire business models. Last week, I published my view that AI is far more likely to be a productivity revolution than an economic collapse. But what does this mean specifically for marketplaces? Many founders are asking: •    Will LLMs capture discovery? •    Will AI compress take rates? •    Will traffic shift away from platforms? •    How defensible are marketplaces in an AI-native world? In this upcoming episode, I break down: •    Why most fears around AI disintermediating marketplaces are overstated. •    Where AI does threaten marketplace margins. •    The structural advantages marketplaces retain. •    The immediate opportunities AI creates for liquidity, cross-border trade, and profitability. •    What founders should do now. If you're building, investing in, or operating a marketplace, this episode is for you!

    58 min

  3. 19 JAN

    #51 Zach Resnick, Founder & CEO of Ascend

    I had the pleasure of chatting with Zach Resnick, the founder and CEO of Ascend (formerly FlyFlat), a membership program for frequent travelers that eliminates 90% of travel decisions and saves 35% off biz/first class flights. Ascend has been helping my partners Jose and Jeff with all their travels for a couple years now, saving FJ Labs over six figures since we first learned about them. Prior to starting Ascend, Zach opened hundreds of credit cards, manufactured over $100M in credit card spend, and started three other travel companies. In addition, he started a crypto hedge fund and a blockchain and fintech-focused venture fund. We covered the following: •    How he opened 300 credit cards. •    Tips to save lots of $ on travel with miles and points. •    Why as a former VC Ascend hasn't raised much capital. •    How to save time and be healthier when traveling long-haul.

    41 min

  4. 20/06/2025

    #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.

    48 min

  5. 09/06/2025

    #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.

    52 min

  6. 22/04/2025

    #48 Ask Me Anything

    I had not done an Ask Me Anything session in over a year which led to many questions on a wide variety of topics: macro, marketplaces, AI, fundraising, wealth management, education, island shopping, India, how to lose your accent, adventure travel, climate tech, the state of VC, and much more. Here are the key questions we covered: 00:01:17 How will all the geopolitical changes, tariffs, and Trump policies influence the world? 00:06:14 What are the key tips for finding and persuading investors? 00:08:44 What do you think is the future of fashion marketplaces? How has it been impacted by downfalls of marketplaces such as Farfetch? What is the role of AI in these? 00:13:19 What's your view on the best investment opportunities currently? Is the stock market, given the current drop off, attractive or still overvalued? I read a while ago your non-traditional approach to wealth management. How would you allocate $10 million now? 00:19:21 We have around 15K revenues per month, are we okay to raise a pre-seed?  00:21:14 What kind of education, school, university degrees do you recommend for kids to best prepare for them for the jobs market in 10 years considering the impact of AI? What skills should they start developing?   00:26:46 What is the best cold inbound email you ever received? 00:29:39  If you're finishing your studies today, what kind of job or company would you join to best train yourself to launch a tech startup later? Is a place like McKinsey or investment banking still relevant if the goal is to learn to work with intensity and structure? 00:32:40 As a recent French graduate with a background in BA in finance, which countries do you think offer the most learning opportunities today in terms of ease of doing business, networking, potential, etc.? 00:33:34 When will you launch the updated and new version of Fabrice AI? How can I build a network in the tech community in France? 00:38:30  Fabrice, any exciting travel coming up? What's your favorite personal use of AI? 00:42:39 If an incumbent exists in my category, are there still opportunities to enter the market? 00:45:51 What made you decide for Turks & Caicos and not another island 00:52:57 What is your favorite place in India? 00:55:48  How did you lose your French accent? What is your secret? 01:00:52 What is on your target list for climate related investment opportunities? 01:02:55  Did you do your long hike through Greenland that you wanted to do? 01:06:03 If you were building a tech company like Zingy today, would you still raise VC money or bootstrap it considering there are many examples of founders barely making any money in $500M exits? 01:08:39 What advice do you have for a home care marketplace founder who has found product market fit but ran out of money in 2023 but has "survived"? 01:10:55 What are the future big trends in AI and especially with consumer usage? 01:13:12  For personal or small retail, which AI tools do you believe are worth paying a subscription for today? 01:13:49 What do you seek in founders for pre-revenue Startups? 01:14:34 What is the biggest turn down for the VC while seeing the pitch deck? What is the biggest green flag as well? What is the red flag when cold connecting with VC people? 01:16:17 Can you address the opportunities for crossover funds? 01:18:43  Any view on Indian VC opportunities? 01:19:29 Should I hire a CTO or CFO? 01:20:23 What do you see as the future for companies like Alan (French Unicorn) nearly 10 years in €500 million raised, still unprofitable, operating on tight margins, valued at €4.5B? 01:21:15 From your perspective, what skill or type of service is the easiest to sell today is a freelance consultant?  01:22:20 How much will Bitcoin be worth in 2030?   01:26:35  What do you think of initiatives such as WorldCoin? 01:26:43  Loved the shoot-out story in the Dominican Republic. Do you have any other crazy adrenaline pumping stories from your adventures? 01:30:27 Do you prefer repeat founders or first-time founders? 01:32:22 Why is it so hard to raise capital for fashion marketplaces?  01:33:28 In your view, what is the most important trait or skill for a founder - being emotionally stable, able to handle the extreme stress, something else entirely? 01:36:11 Would you be open for a lunch in New York so I can bring all the questions I have for 45 minutes? 01:37:13 What makes niche marketplaces breakout and go big globally? 01:39:44 Is artificial intelligence dangerous for humanity? Will it increase unemployment? Should countries create rules to prevent that? Can we master something that might be beyond us? 01:46:46 What's your take on vibe coding trend or real shift?

    1h 48m

  7. 16/12/2024

    #47 Marketplace Trends

    Given that I have been building and investing in marketplaces for 26 years you might think that everything that needed to be built has already been built, but nothing could be further from the truth. In many ways, we are still at the beginning of the marketplace revolution with lots of exciting new trends. In this episode, I cover:  Cross border commerce. Live commerce. New goods verticals supported by service layers. High take rate business models based on convenience. Climate tech. AI enabled marketplaces. B2B marketplaces: Marketplace for inputs. SMB enablement. Friendshoring. B2B labor marketplaces. Business infrastructure. B2B recommerce. The episode was highly interactive with dozens of audience questions. Here are some of the questions that I answered: What types of marketplaces can function in real estate? What are the valuation multiples I am seeing at investment and exit? What is the best platform to build a marketplace on?

    56 min

  8. 18/11/2024

    #46 FJ Labs' AI Thesis

    While AI investing continues to reach new highs, we have been contrarian. Given how non-consensus we are, I wanted to share our thoughts and perspective.  In this episode, I cover: The general state of venture. The explosion in AI investing.  The varying fortunes of AI startups. FJ Labs' perspective on AI. FJ Labs' AI investments.  The episode was highly interactive with dozens of audience questions. Here are some of the questions that I answered: How is AI impacting sports, especially tennis from an entertainment and industry standpoint? How are you utilizing AI in your personal life to improve your processes? Which tools? What is your recommendation towards founders or technology enthusiasts about AI that want to explore technological solutions using AI or find funding? How will AI help secondhand fashion marketplaces? How will labor marketplaces be impacted by AI? How will AI impact the media industry? What is my perspective on how AI and AR will be combined to create better experiences? What are examples of picks and shovels companies we are investing in to benefit from the AI boom? How to address sellers' fears that AI will make it harder for them to compete effectively with other sellers in the marketplace? Which roles will be most impacted by AI? Will it cause mass unemployment? Will AI amplify the best or worst traits of humanity? How will AI impact healthcare and education? What should startups focus on in terms of implementing AI: customer service, product search or other?

    1h 14m
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About

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.

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