Delusional Podcast

#12 Ringing the NASDAQ IPO bell [$1b] to building the 'OG' fintech VC firm, with Jake Gibson [BTV]

38 min · 27. nov. 2025
episode #12 Ringing the NASDAQ IPO bell [$1b] to building the 'OG' fintech VC firm, with Jake Gibson [BTV] cover

Description

Jake Gibson is a co-founder and GP at Better Tomorrow Ventures, Silicon Valley's coolest early stage fintech VC firm. Previously, he co-founded NerdWallet, a $1b publicly listed company.Timestamps:00:00 - In this episode01:00 - Introduction03:04 - Inception of Nerdwallet, not taking VC money, building a marketing machine07:36 - Ringing the NASDAQ IPO bell and being a small part of something meaningfully big09:20 - Leaving a lot of money on the table to be a present parent to his twins11:52 - Using angel investing as a forcing function to figure out what to do next in life 14:57 - Teaming up with Sheel as a co-GP, complementary profiles, perfect match?19:09 - Low egos and how to manage friction between GPs20:58 - Raising Fund1, harder than expected. Fund2? Super easy. Fund3, hard again. 24:17 - Investing in the best founders, regardless of geography: Brazil, Saudi, Nigeria26:08 - Why is Jake bullish on Brazil?28:29 - The brain switch required to invest in emerging markets vs. in the US30:20 - How to keep a fresh mind when you've 'seen it all'?34:10 - Is fintech really only 1% built? or are we close to saturation?36:34 - How to blindly invest in the AI era when nobody knows what the world will look like?References:Nerdwallet - https://www.reuters.com/article/technology/startup-nerdwallet-raises-64-million-in-first-round-of-funding-idUSKBN0NW25G/Jake's partner Sheel - https://mercury.com/blog/sheel-mohnotAbout Cauridor [sponsor]:Cauridor is connecting businesses to a continent of payment opportunities. They’re building the payment rails across Africa to enable companies to process money transfers and payments to, from, and within the continent through a single API integration. With market-beating exchange rates and dedicated customer support teams on the ground, Cauridor empowers its partners to deliver a seamless and competitive payment journey to customers throughout Africa. For more info, visit: www.cauridor.comAbout OmniRetail [sponsor]:OmniRetail is a unified commerce company transforming how manufacturers, distributors, and retailers across Africa connect, trade, and access finance. Through its product suite (Omni One (manufacturer OS), OmniHub (distributor OS), OmniBiz (retailer OS), and OmniPay (embedded finance)) the company digitizes the entire B2B commerce chain, enabling smarter distribution, faster payments, and inclusive growth for small businesses. Operating across Nigeria, Ghana, and Côte d’Ivoire, OmniRetail is building Africa’s largest connected supply network for everyday essentials. For more info, visit: www.omniretail.africaListen on all platforms:Youtube - ⁠https://www.youtube.com/@TheDeluluPodSpotify - ⁠https://open.spotify.com/show/3vUDH5yEH6pvRkqM1TVaxS⁠Apple Podcasts - ⁠https://podcasts.apple.com/ca/podcast/the-rally-cap-podcast/id1731710244⁠Where to find Jake:Linkedin: https://www.linkedin.com/in/jacobgibson/X/Twitter: https://x.com/iamjakestreamWhere to find Kyane:Linkedin: https://www.linkedin.com/in/kyanekassiriX/Twitter: https://twitter.com/kyanekassiri

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14 episodes

episode #14 A healthy and balanced founder is less likely to build a massive company, w/ Sheel Mohnot [BTV] artwork

#14 A healthy and balanced founder is less likely to build a massive company, w/ Sheel Mohnot [BTV]

Sheel Mohnot is the co-founder of Better Tomorrow Ventures, one of Silicon Valley's favorite fintech investors. Previously, he built FeeFighters [acquired by Groupon], Innovative Auctions, and Thistle while having angel invested in companies such as Ramp, Flexport, and Mercury. Timestamps: 00:00 - In this episode 01:29 - Introduction 03:33 - First liquidity event $$$: selling Fee Fighters to Groupon 08:37 - Building a cash-cow business leveraging ICANN auctions 12:13 - Does Sheel 'add value' for his portfolio founders? 15:58 - VCs = master manipulators? 18:29 - Great investments he wouldn't have made if he knew better 20:14 - The nature of the game rewards unbalanced founders 21:51 - Teaming up with a polar-opposite business partner 23:52 - Difficult fundraise despite the past successes - what LPs wanted to see 25:58 - The reason BTV will become less active in emerging markets 28:48 - Investing in IndiaGold in India, and BRKZ in Saudi 31:51 - Winning competitive deals against giant firms dropping term sheets 33:43 - Businesses Sheel isn't excited about + my contrarian opinion 35:09 - Are your 'work friends' real friends? founders, co-investors, etc 36:22 - Sheel's aspiration post-retirement [take a guess] References: IndiaGold - https://techcrunch.com/2021/08/26/indiagold-raises-12-million-for-its-gold-focused-digital-alternative-credit-platform BTV raises Fund 3 - https://techcrunch.com/2025/10/01/better-tomorrow-ventures-closes-140m-remains-bullish-on-fintech Sheel Mohnot - https://mercury.com/blog/sheel-mohnot About Cauridor [sponsor]:Cauridor is connecting businesses to a continent of payment opportunities. They’re building the payment rails across Africa to enable companies to process money transfers and payments to, from, and within the continent through a single API integration. With market-beating exchange rates and dedicated customer support teams on the ground, Cauridor empowers its partners to deliver a seamless and competitive payment journey to customers throughout Africa. For more info, visit: www.cauridor.com About OmniRetail [sponsor]:OmniRetail is a unified commerce company transforming how manufacturers, distributors, and retailers across Africa connect, trade, and access finance. Through its product suite (Omni One (manufacturer OS), OmniHub (distributor OS), OmniBiz (retailer OS), and OmniPay (embedded finance)) the company digitizes the entire B2B commerce chain, enabling smarter distribution, faster payments, and inclusive growth for small businesses. Operating across Nigeria, Ghana, and Côte d’Ivoire, OmniRetail is building Africa’s largest connected supply network for everyday essentials. For more info, visit: www.omniretail.africa Listen on all platforms: Youtube - ⁠https://www.youtube.com/@TheDeluluPodSpotify - ⁠https://open.spotify.com/show/3vUDH5yEH6pvRkqM1TVaxS⁠Apple Podcasts - ⁠https://podcasts.apple.com/ca/podcast/the-rally-cap-podcast/id1731710244 ⁠Where to find Sheel: Linkedin: https://www.linkedin.com/in/smohnot X/Twitter: x.com/pitdesi Where to find Kyane: Linkedin: https://www.linkedin.com/in/kyanekassiri X/Twitter: x.com/kyanekassiri

1. feb. 202637 min
episode #12 Ringing the NASDAQ IPO bell [$1b] to building the 'OG' fintech VC firm, with Jake Gibson [BTV] artwork

#12 Ringing the NASDAQ IPO bell [$1b] to building the 'OG' fintech VC firm, with Jake Gibson [BTV]

Jake Gibson is a co-founder and GP at Better Tomorrow Ventures, Silicon Valley's coolest early stage fintech VC firm. Previously, he co-founded NerdWallet, a $1b publicly listed company.Timestamps:00:00 - In this episode01:00 - Introduction03:04 - Inception of Nerdwallet, not taking VC money, building a marketing machine07:36 - Ringing the NASDAQ IPO bell and being a small part of something meaningfully big09:20 - Leaving a lot of money on the table to be a present parent to his twins11:52 - Using angel investing as a forcing function to figure out what to do next in life 14:57 - Teaming up with Sheel as a co-GP, complementary profiles, perfect match?19:09 - Low egos and how to manage friction between GPs20:58 - Raising Fund1, harder than expected. Fund2? Super easy. Fund3, hard again. 24:17 - Investing in the best founders, regardless of geography: Brazil, Saudi, Nigeria26:08 - Why is Jake bullish on Brazil?28:29 - The brain switch required to invest in emerging markets vs. in the US30:20 - How to keep a fresh mind when you've 'seen it all'?34:10 - Is fintech really only 1% built? or are we close to saturation?36:34 - How to blindly invest in the AI era when nobody knows what the world will look like?References:Nerdwallet - https://www.reuters.com/article/technology/startup-nerdwallet-raises-64-million-in-first-round-of-funding-idUSKBN0NW25G/Jake's partner Sheel - https://mercury.com/blog/sheel-mohnotAbout Cauridor [sponsor]:Cauridor is connecting businesses to a continent of payment opportunities. They’re building the payment rails across Africa to enable companies to process money transfers and payments to, from, and within the continent through a single API integration. With market-beating exchange rates and dedicated customer support teams on the ground, Cauridor empowers its partners to deliver a seamless and competitive payment journey to customers throughout Africa. For more info, visit: www.cauridor.comAbout OmniRetail [sponsor]:OmniRetail is a unified commerce company transforming how manufacturers, distributors, and retailers across Africa connect, trade, and access finance. Through its product suite (Omni One (manufacturer OS), OmniHub (distributor OS), OmniBiz (retailer OS), and OmniPay (embedded finance)) the company digitizes the entire B2B commerce chain, enabling smarter distribution, faster payments, and inclusive growth for small businesses. Operating across Nigeria, Ghana, and Côte d’Ivoire, OmniRetail is building Africa’s largest connected supply network for everyday essentials. For more info, visit: www.omniretail.africaListen on all platforms:Youtube - ⁠https://www.youtube.com/@TheDeluluPodSpotify - ⁠https://open.spotify.com/show/3vUDH5yEH6pvRkqM1TVaxS⁠Apple Podcasts - ⁠https://podcasts.apple.com/ca/podcast/the-rally-cap-podcast/id1731710244⁠Where to find Jake:Linkedin: https://www.linkedin.com/in/jacobgibson/X/Twitter: https://x.com/iamjakestreamWhere to find Kyane:Linkedin: https://www.linkedin.com/in/kyanekassiriX/Twitter: https://twitter.com/kyanekassiri

27. nov. 202538 min
episode RCP #12 The African AI pioneer who sold his company for $700m, with Karim Beguir [InstaDeep] artwork

RCP #12 The African AI pioneer who sold his company for $700m, with Karim Beguir [InstaDeep]

Karim Beguir is the co-founder and CEO of InstaDeep, a Tunisia/Africa-born company that grew into a global deep-tech AI powerhouse and got acquired by german biotech giant BioNTech for $700m.Timestamps:00:00 - In this episode00:53 - Introduction01:42 - Modeling protein folding with AI08:26 - Solving combinatorial optimization with AI12:58 - Identifying upcoming COVID variants with AI17:06 - Curing cancer with mRNA and AI?20:19 - Consulting model vs VC-backed startup?22:11 - From academic curiosity to commercialization24:30 - Overcoming the disadvantage of building from Africa27:09 - The upside of building from Africa29:01 - The reasoning behind partnering with BioNTech31:30 - Raising a Series C or getting acquired?35:01 - Preserving InstaDeep's DNA post-acquisition36:19 - Staying grounded despite fame, money, success37:43 - Making a lot of money messes with your brain?40:21 - What does Karim wanna do now?42:08 - Africa's role in the AI race45:59 - Karim's mistake46:55 - Karim's hardest decision47:21 - Karim's favorite (non-famous) founder47:42 - How to allocate a $100m investment in African tech?50:07 - Advice to African founders building in deep techReferences:Karim's book: 'LEAPFROG' - https://www.amazon.com/LEAPFROG-Building-Africas-Future-Era-ebook/dp/B0F2JBYB8DInstaDeep's research portal - https://instadeep.com/research/Nature Machine Intelligence's feature - https://www.nature.com/natmachintell/volumes/7/issues/6Listen on all platforms:Youtube - ⁠https://www.youtube.com/@TheRallyCapPodcastSpotify - ⁠https://open.spotify.com/show/3vUDH5yEH6pvRkqM1TVaxS⁠Apple Podcasts - ⁠https://podcasts.apple.com/ca/podcast/the-rally-cap-podcast/id1731710244⁠Where to find Karim:Linkedin: https://www.linkedin.com/in/karim-beguir-2350161/X/Twitter: https://x.com/kbeguirWhere to find Kyane:Linkedin: https://www.linkedin.com/in/kyanekassiriX/Twitter: https://twitter.com/kyanekassiriLearn more about Rally Cap: https://techcrunch.com/2022/05/05/rali_cap-gets-backing-from-global-vcs-and-launches-30m-fintech-fund-for-emerging-markets/

24. aug. 202550 min
episode RCP #11 Backing Uber, Airbnb, Spotify (w Man Cap) then going all-in on Africa, with Hisham Halbouny artwork

RCP #11 Backing Uber, Airbnb, Spotify (w Man Cap) then going all-in on Africa, with Hisham Halbouny

Hisham Halbouny is a managing partner at P1 Ventures, a $50m Africa-focused fund who's often referred to as contrarian. Hisham was previously a partner at Man Capital, the family office of Egyptian Billionaire Mohamed Mansour where he invested in Uber, Airbnb, Spotify, Bolt, and more.Timestamps:00:00 - In this episode00:36 - Introduction01:13 - Investing in Uber/Airbnb/Spotify03:16 - Going all-in on Africa06:20 - Global VCs have pulled back, yet the timing is right07:43 - DFIs as the default LPs for African VC?08:54 - Tailoring the VC model for Africa?13:03 - P1's investment thesis16:33 - Personal evolution as an investorReferences:P1 Ventures - https://techcrunch.com/2023/09/26/pan-african-contrarian-investor-p1-ventures-reaches-25m-first-close-for-its-second-fund/Man Capital - https://www.man-capital.com/DFIs coming to the rescue - https://techcabal.com/2023/06/05/role-of-dfis-in-africa-ecosystem/Listen on all platforms:Youtube - ⁠https://www.youtube.com/@TheRallyCapPodcastSpotify - ⁠https://open.spotify.com/show/3vUDH5yEH6pvRkqM1TVaxS⁠Apple Podcasts - ⁠https://podcasts.apple.com/ca/podcast/the-rally-cap-podcast/id1731710244⁠Where to find Hisham:Linkedin: https://www.linkedin.com/in/hisham-halbouny-7a5ba23/Where to find Kyane:Linkedin: https://www.linkedin.com/in/kyanekassiriX/Twitter: https://twitter.com/kyanekassiriLearn more about Rally Cap: https://techcrunch.com/2022/05/05/rali_cap-gets-backing-from-global-vcs-and-launches-30m-fintech-fund-for-emerging-markets/

24. juli 202519 min
episode RCP #10 Selling Expensya for $100m 😱💰, with Karim Jouini [ThunderCode] artwork

RCP #10 Selling Expensya for $100m 😱💰, with Karim Jouini [ThunderCode]

Karim Jouini is the founder of Expensya, an expense management platform sold to Medius Group for $100m. Karim is now building his second company called ThunderCode: an AI testing agent for software teams.Timestamps:00:00 - In this episode01:58 - Introduction02:59 - Missing PMF, SMB sucks, pivot to mid-market06:03 - Brex, Ramp, & copycats in Africa/LatAm/Asia10:31 - Karim's new AI company16:55 - Expensya: industry evolution, black swan event25:42 - Selling to corporates, build vs. buy, competition 31:01 - North star metrics, improvising, burn-outs, failed PoC38:45 - What takes you to $3m ARR won't take you to $10m ARR43:49 - Decision to sell, acquisition process, price discovery, etc49:37 - Secrets behind "Build locally, sell globally" [Tunisian playbook]54:32 - Personal: Making a lot of money... & building again References:Expensya's acquisition - https://www.medius.com/news/cid-B5994B54FD438614/media-alert-medius-completes-acquisition-of-expense-management-firm-expensya/Brex exists SMB space - https://techcrunch.com/2022/06/17/as-brex-exits-the-smb-space-its-ceo-says-that-doesnt-include-startups-at-least-the-funded-ones/What would Google Do? https://aszapla.wordpress.com/wp-content/uploads/2011/12/what-would-google-do.pdfListen on all platforms:Youtube - ⁠https://www.youtube.com/@TheRallyCapPodcastSpotify - ⁠https://open.spotify.com/show/3vUDH5yEH6pvRkqM1TVaxS⁠Apple Podcasts - ⁠https://podcasts.apple.com/ca/podcast/the-rally-cap-podcast/id1731710244⁠Where to find Karim:Linkedin: https://www.linkedin.com/in/karimjouini/X/Twitter: https://x.com/karim_jouiniWhere to find Kyane:Linkedin: https://www.linkedin.com/in/kyanekassiriX/Twitter: https://twitter.com/kyanekassiriLearn more about Rally Cap: https://techcrunch.com/2022/05/05/rali_cap-gets-backing-from-global-vcs-and-launches-30m-fintech-fund-for-emerging-markets/

25. mar. 20251 h 2 min