Pocket Sun’s Guide to Standing Out as an Emerging Investor

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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 startup05:30 – Angel investing isn’t just for the ultra-wealthy09:45 – From building a global pitch comp to proving LP credibility14:20 – Early wins: Everly Health, Lovevery, and chasing allocation23:35 – “Land and expand”: getting on cap tables and earning super pro-rata27:10 – Leading recaps and fighting for underestimated founders35:00 – SoGal’s thesis: The future of living, working, and staying healthy40:30 – Entering new verticals without prior expertise46:00 – Pocket’s take on the Vancouver vs. Toronto startup ecosystems53:00 – Betting on design-led, intentional consumer businesses59:10 – Why consumer startups often graduate into enterprise giants01:03:00 – Pocket’s Big Cojones moment: moving solo to the U.S. at 18Resources🙋‍♀️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___Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman.As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs.The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business.As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/peartreeFirst 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 1FC Vanta Ad March 2025_02FC Vanta Ad March 2025_02This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/