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.
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#51 Zach Resnick, Founder & CEO of Ascend
01/19/2026
#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.
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#50 Venture Market Trends
06/20/2025
#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.
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#49 Dan Park and the Incredible Comeback Story of Clutch
06/09/2025
#49 Dan Park and the Incredible Comeback Story of 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.
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#48 Ask Me Anything
04/22/2025
#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?
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#47 Marketplace Trends
12/16/2024
#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?
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#46 FJ Labs’ AI Thesis
11/18/2024
#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?
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#45 Ask Me Anything
04/10/2024
#45 Ask Me Anything
I had not done an Ask Me Anything (AMA) session in over a year which led to many questions on a wide variety of topics: AI, augmented reality, crypto, macro and much more. Here are the key questions we covered: • 00:01:44 Artificial Intelligence: Where are we now? Where are we heading? What is the timeline? Why is FJ Labs a way contrarian on the AI trend? • 00:09:42 What's your perspective on augmented reality? Is the Apple Vision Pro a revolution? And what is the timing for that to filter into our day-to-day life? • 00:15:28 What was the fundamental inspiration for me to start OLX? • 00:20:45 Can you give us some context or details on Midas? • 00:23:15 Is there any way for a small retail investor to invest in early financing rounds for startups? If yes, how? • 00:24:44 At for pre-seed rounds, what should be the GMV to get your attention? Let's say a new marketplace. What GMV would be impressive in the first month, six months, and one year? • 00:25:39 What do I expect to see at the seed round? • 00:26:41 What’s the correct take rate? • 00:27:56 What are my current perspectives on the crypto market? • 00:34:43 Does FJ Labs have an activist approach when investing in startups? How are you supporting the founders? • 00:38:03 Is there going to be a fiat currency crisis where the dollar will be replaced? Will something like BTC become the reserve currency? • 00:41:18 Have you decided on your next adventure for outdoor travel that you'd like to tackle? • 00:43:11 I've heard that a startup should recoup their fully loaded Customer Acquisition Cost (CAC) within 6 months based on the contribution margin and then triple that amount within 18 months. Could you confirm if these numbers are accurate? • 00:44:30 What should the first 3-6 months of a new startup look like? Talk to potential customers? Generate demand? Build a prototype? Validate hypotheses? Etc. • 00:46:33 Does FJ Labs have an anti-portfolio? • 00:50:28 Do you have any thoughts on the longevity industry? Do you think platforms like Hims or Ro will evolve in that direction, or will there be a new player? • 00:53:33 I’ve listed things that I heard you consider when rating a startup. (1.) Team (2.) Unit Economics, significant TAM (3.) Fair deal terms, reasonable valuation, (4.) is it beneficial to the world, aligning the general direction of global trends, offering new opportunities to those with fewer opportunities. Is there anything else? • 00:55:02 What build did I play at Elden Ring? • 00:56:00 Did you have any mentor in your angel investor career? If yes, who is it? And how does the person help you? • 00:58:49 Are you tempted to invest in AI? • 01:00:08 What’s the most overused buzzword that you can't stand? • 01:00:37 What valuation of a company is risky, yet a bit safe and worth the squeeze? • 01:01:27 Any particular places or people you prefer to keep up with your bio health updates? • 01:02:38 What is a surprisingly cheap and effective marketing channels? • 01:03:50 As an investor, doesn't make sense to look for opportunities other than AI even though AI is “hot” now? • 01:05:53 What are the most incredible business opportunities you have seen in preventative health lately? • 01:07:04 Can you name successful blockchain based marketplaces that work with goods other than NFTs? •01:11:39 Regarding Firgure.ai, when, in your opinion will we see humanoid robots in our daily lives? 3 years? 5 years? 20 years? •01:14:15 Do you think asteroid mining is an industry that will become feasible or profitable within our lifetime? • 01:16:08 We continue to see economic sentiment down, given the cost of money felt by consumers. Curious, given how you feel, especially the dire US consumers in Macroeconomic update where you see bright falls, bright spots in the landscape? • 01:19:35 Whom do you think had the most impact on your investing thesis? • 01:21:16 Is there something you've seen in recent startup pitches that you think the general public should know? • 01:23:00 When it comes to crypto, how game changing do you consider the ETFs to be going forward? • 01:24:22 What is the ideal number of founders per startup? Two, with one being technically oriented the other more focused on people and sales? • 01:25:43 What are the most important skills that students should develop in order to work as an analyst in a VC fund? What are the qualities you're looking for when recruiting graduates? • 01:27:34 If you live in a different time past or present, what do you think you would do professionally or future? • 01:32:08 My main competitor received ~$200 million in recent debt round in 2021, and $490 million in 2019 led by SoftBank. I think that's a good sign for me because they started 2007. • So now they're too big and too slow. My startup is like a small pirate ship that can easily change direction, add new features, et cetera. Am I wrong? • 01:36:54 Investing in France: What do you think of the system? • 01:37:48 What do you think of digital biology? • 01:38:41 With your milestone birthday coming up, I can't wait. What adventurous ambitions are you most looking forward to in the next half century? • 01:40:14 What is the dream guest you would like to have on the Playing with Unicorn podcast and why? • 01:44:58 Can you share the acceptance percentage of FJ Labs for the pre-seed and seed rounds? What are the chances that you will be invited to poll with your team? • 01:47:53 What is the last job to be replaced by AI robots?
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#44 Unlocking Productivity: Streamlining Your Days for Passion and Purpose
01/11/2024
#44 Unlocking Productivity: Streamlining Your Days for Passion and Purpose
People often ask me how I manage to accomplish so much while leading such a rich, passionate life as illustrated by . In this episode I share all my secrets. I will cover everything from general productivity tips to how and what you can outsource in your professional and personal life.
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#43 Julio Vasconcellos and the state of Latin American tech
09/10/2023
#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 , 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.
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#42 Kevin Ryan, Unicorn Builder
03/17/2023
#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.
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Episode 41: Ask Me Anything
02/12/2023
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.
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#40 Oskar Hartmann: Unicorn Accumulator
12/20/2022
#40 Oskar Hartmann: Unicorn Accumulator
This week, I had the pleasure of chatting with my good friend Oskar Hartmann. He’s had the most incredible unicorn experience: He was part of 10% of all German unicorns Made a $300M mistake on Ozon Managed to make money on Fab.com despite it going from $1.5B in value to $0 in 6 months Why selling at the point of maximum secondary liquidity is probably a bad time to sell Much more!
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#39: Simpl and the Indian Fintech Ecosystem
12/20/2022
#39: Simpl and the Indian Fintech Ecosystem
On this week’s episode I had the pleasure of welcoming Nitya Sharma, co-founder and CEO of , to conclude our mini-series on the Indian tech scene. We had a fascinating conversation on the state of Indian Fintech, which in many ways is more advanced than the US. I am beyond impressed by the free C2C / B2B / B2C instantaneous real time payments allowed by UPI and the business models that emerge when you can do free microtransactions. I wish the West had the equivalent of India’s UPI (or Brazil’s Pix). I am also beyond impressed by what Nitya has built with Simpl, which I hope will be a Unicorn soon!
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#38 The Indian Tech Ecosystem & FJ Labs’ Thesis in the region
10/13/2022
#38 The Indian Tech Ecosystem & FJ Labs’ Thesis in the region
This week we are covering the state of the Indian tech ecosystem. We are joined by Luke Skertich, senior associate at FJ Labs, who is leading the charge with our Indian investments. In this episode, we cover: The history of India’s tech ecosystem and the recent explosion in unicorns Why we are short term pessimistic, but medium and long term super bullish Why we are focusing on Picks and Shovels, Financial Infrastructure, and B2B Marketplaces
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#37 Building India's 76th Unicorn & the Indian car market at large
10/10/2022
#37 Building India's 76th Unicorn & the Indian car market at large
In this episode, we cover: Niraj’s path to creating Spinny, including creating two much less successful startups right out of college The differences between the US & Indian car markets Spinny’s unique solution to the market considering the specifics of the market Spinny’s ambitions on a go forward basis The impact, if any, of the massive global multiple compression in comps like Carvana and Cazoo The state of Indian tech market
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#36 Building a Web3 Unicorn with Lorien Gabel (Figment)
03/20/2022
#36 Building a Web3 Unicorn with Lorien Gabel (Figment)
Lorien Gabel is the Co-Founder of Figment Network. He holds an LLB from Toronto’s Osgoode Hall Law School and is a member in good standing with the Ontario Bar. In 1994, at the age of 24, 6 months into practicing law, Lorien quit to help his brother Matt run a bourgeoning internet company, Interlog. Over the next four years, they managed the growth of Interlog to over 150 employees, 65,000 customers and profitability. It was later acquired by a large multinational telecommunications company.
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#35 Thoughts on the market
02/15/2022
#35 Thoughts on the market
These days every meeting seems to start with a conversation on market conditions. In the next episode, I am sharing my perspective on what has been happening in the public, crypto, and private markets, and what it means for investors and founders.
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#34 Ask Me Anything
02/14/2022
#34 Ask Me Anything
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#33 From VC to Web2 to Crypto with Mark Lurie
02/13/2022
#33 From VC to Web2 to Crypto with Mark Lurie
Mark Lurie is the CEO and co-founder of . Shipyard Software builds decentralized exchanges (DEX) for specific types of trades, traders, and instruments, starting with , a DEX with the best prices anywhere on retail trades
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#32 Building a shipping unicorn with Laura Behrens Wu, Co-Founder & CEO of Shippo
11/24/2021
#32 Building a shipping unicorn with Laura Behrens Wu, Co-Founder & CEO of Shippo
Laura Behrens Wu is the co-founder and CEO of Shippo. Shippo is an API-first company focused on building shipping for 21st-century e-commerce. Top takeaways Build something that’s a pain killer, not a vitamin. This means finding a true pain point and solving it. Constantly seek new customer acquisition channels. Keep in mind that people who succeed at corporations are not always successful at early-stage companies. 0-1 team members are not always the ones who will drive the company to 100x.
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#31 From Start-up to Grown-up with Alisa Cohn
11/24/2021
#31 From Start-up to Grown-up with Alisa Cohn
Alisa Cohn () is a prominent startup coach who has advised founders and executives at Venmo, Etsy, DraftKings, The Wirecutter, Mack Weldon, and Bloomberg. She’s one-time startup CFO, strategy consultant, and current angel investor and advisor, she was named the number one “Global Guru”. Her articles have appeared in HBR, Forbes, and Inc and she has been featured as an expert on Bloomberg TV, the BBC World News and in the New York Times. A recovering CPA, she is also a Broadway investor in productions which have won two Tony Awards and is prone to burst into song at the slightest provocation.
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#30 A Conversation with Thomas Plantenga
11/10/2021
#30 A Conversation with Thomas Plantenga
Thomas Plantenga is the CEO of Vinted. He was born and raised in the Netherlands. Thomas was previously a Venture Partner at FJ Labs and an early member of OLX. Thomas never intended to join Vinted. He flew from New York to Vilnius for 5 weeks to simply to have a deeper look at Vinted’s metrics. At the end of the 5th week, Thomas proposed an aggressive plan to the team, and to his surprise the team accepted. It was here Thomas knew that the Vinted team was committed to succeeding no matter what. Over the past decade, Thomas has lived in: Amsterdam, São Paulo, Buenos Aires, Nairobi, Cabarete, Barcelona, and New York.
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#29 The Latest Marketplace Trends
09/22/2021
#29 The Latest Marketplace Trends
In episode 27, I took a stab at which categories investors and entrepreneurs should focus on for the coming 5 years. In today’s episode, I wanted to cover the themes and trends that emerged in the last 12 months. Ten trends clearly emerged as we saw them time and time again with a plethora of competitors in every geography. There was no unifying theme across all of them, but four of the trends cover startups that help SMBs and micro-entrepreneurs run their businesses better allowing their owners to focus on what they do best.
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#28 What's the deal with crypto
08/05/2021
#28 What's the deal with crypto
When Satoshi Nakamoto famously wrote the Bitcoin white paper on November 13, 2008 it proposed to solve the Byzantine Generals problem. The Byzantine Generals Problem is solving the puzzle of how multiple, separated generals can achieve consensus on the time to attack a particular city.
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#27 The Tech Of Tomorrow
07/30/2021
#27 The Tech Of Tomorrow
In a way I live in your future. By virtue of receiving 150 startup pitches per week, I have a good sense of what founders are trying to build for the coming decade.
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#26 Jeff Wald & The End of Jobs
06/25/2021
#26 Jeff Wald & The End of Jobs
Jeff’s newest book, The End of Jobs: The Rise of On-Demand Wokers and Agile Corporations, provides a look into the future of work by looking into the past. In human history, there have been three monumental technological revolutions: mechanization, electrification, and computerization. These revolutions shaped the future of humanity. Jeff shows the end of work will be a good thing for humanity because it will free up time and allow humans to do creative work.
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#25 Clearco & the future of SMB lending
06/16/2021
#25 Clearco & the future of SMB lending
As most of you know, I want to empower people to work on the things they love. As a result, I am excited that FJ Labs invested early in Clearco (formerly Clearbanc), now valued at $2 billion, which is helping entrepreneurs all around the world to live out their dream.
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#24 How Slice is helping mom-and-pop pizzerias compete with Dominos
05/21/2021
#24 How Slice is helping mom-and-pop pizzerias compete with Dominos
One of our main theses at FJ Labs is to focus on vertical marketplaces. Slice is a great example of a company that has found product-market fit within a vertical.
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#23 Synthesis: The startup scaling up the most innovative ideas from Elon Musk's school
05/15/2021
#23 Synthesis: The startup scaling up the most innovative ideas from Elon Musk's school
The education system has not evolved since the industrial era. New tools have been introduced over the years, but nothing has dramatically changed. To reinvent education, you don’t more tools to add to the arsenal, but first principal thinking. What assumption have we been making about education? And are these assumptions true?
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#22 Why Startups Fail with Tom Eisenmann
04/26/2021
#22 Why Startups Fail with Tom Eisenmann
9 out of 10 startups fail. This is a gloomy number. However, it has never stopped entrepreneurs from hedging their bets to create successful companies.
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