Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey Episode SummaryPocket Sun is the Founding Partner at SoGal Ventures, the first female-led, millennial VC firm investing in the future of living, working, and staying healthy. In this episode, she shares how she made her first angel investment at just 24, and how her early bets like Everly Health and Lovevery reflected a conviction in underrepresented founders well before it was a trend. Cheryl and Maxine explore how Pocket launched SoGal’s debut fund, built a deal pipeline through global pitch comps and community, and mastered the art of getting onto oversubscribed cap tables. They also unpack her consumer investing thesis, how she’s navigating fund two with more geographic focus, and what it means to lead recaps and board restructures when the power law turns brutal. For anyone curious about building a fund from scratch, going global with limited resources, or backing change-makers the market misses, this episode is packed with both tactics and courage. Time Stamps00:00 – Pocket’s first angel check: $1K into an AI startup 05:30 – Angel investing isn’t just for the ultra-wealthy 09:45 – From building a global pitch comp to proving LP credibility 14:20 – Early wins: Everly Health, Lovevery, and chasing allocation 23:35 – “Land and expand”: getting on cap tables and earning super pro-rata 27:10 – Leading recaps and fighting for underestimated founders 35:00 – SoGal’s thesis: The future of living, working, and staying healthy 40:30 – Entering new verticals without prior expertise 46:00 – Pocket’s take on the Vancouver vs. Toronto startup ecosystems 53:00 – Betting on design-led, intentional consumer businesses 59:10 – Why consumer startups often graduate into enterprise giants 01:03:00 – Pocket’s Big Cojones moment: moving solo to the U.S. at 18 Resources🙋♀️Pocket Sun on LinkedIn – Connect with Pocket and follow her updates. https://www.linkedin.com/in/pocket 💰SoGal Ventures – A VC firm backing diverse founders in the future of living, working, and staying healthy. https://www.sogalventures.com/ Sponsors:First Cheque is supported by our wonderful sponsors:Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. Mentioned in this episode: Deel x PX_Script 1 FC Vanta Ad March 2025_02 FC Vanta Ad March 2025_02 This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/