#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.

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.

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.  

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?

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?

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? 

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?

People often ask me how I manage to accomplish so much while leading such a rich, passionate life as illustrated by my 2023 year in review. 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.

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.

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.