Jane Technologies built real-time inventory streaming technology that connects cannabis dispensary point-of-sale systems to online ordering platforms—solving a technical problem that hadn’t been cracked before in the space. As a West Point graduate and Apache helicopter pilot who found cannabis instrumental in his transition from military service, Socrates co-founded Jane with his brother (a computer scientist) in 2014-2015, deliberately choosing the ”pick and shovel” software play over plant-touching operations. Operating in a market where major VCs won’t invest, credit card networks won’t process payments, NASDAQ won’t list your stock, and regulatory missteps can mean federal charges, Jane developed an extreme discipline around capital efficiency and risk management that offers tactical lessons for any founder building in constrained or emerging markets. Topics Discussed: - Jane’s technical innovation: streaming real-time physical inventory from store shelves to online platforms - Regulatory timing: the Cole Memo, state-by-state legalization momentum, and using adjacent players as risk indicators - Risk taxonomy: creating frameworks to convert market uncertainty into scored, calculable risk decisions - Strategic positioning as infrastructure provider versus licensed operator to manage legal exposure - Customer evolution: illicit market operators meeting institutional players in the middle, and what survives - Capital structure constraints driving operational discipline: no traditional payment rails, no public markets, limited institutional capital - Competitive moat building through regulatory complexity rather than despite it - Jane’s decision framework on legal gray areas and why ”maybe” always means ”no” GTM Lessons For B2B Founders: - Use adjacent players as regulatory canaries, then move decisively - Build compliance infrastructure as a moat, not overhead - Convert uncertainty into scored risk through systematic information gathering - Capital constraints create competitive advantages through forced discipline // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM