The Fork in the Road

What happens when your startup fails overnight?In this episode of The Fork in the Road with Perry S. Kaufman, Tejas Manohar shares how his first company collapsed during COVID… and how that failure led to building a company that has raised over $200 million.Tejas walks through his full founder journey, from teaching himself to code as a teenager to landing a job in Silicon Valley at 16, to building HighTouch, a company transforming how businesses use data and AI.You’ll hear how he:Got hired without revealing his ageFound his first customers through cold outreach and online communitiesPivoted after losing everythingBuilt a product the market started pulling, not pushingScaled from 3 founders to 350+ employeesThis is a real look at what building a company looks like, messy, unpredictable, and driven by persistence.If you’re a founder or thinking about starting, this episode will change how you see the journey.⏱️ TIMESTAMPS0:00 Welcome + Tejas intro1:00 Early obsession with programming2:30 Influence of immigrant parents6:20 How he got hired at 16 (without saying his age)10:30 Learning + dreaming at Segment13:00 Why you don’t need a “perfect idea”16:00 The first startup (and why it failed)18:00 COVID wiped out the business overnight20:00 The pivot that led to HighTouch21:30 What HighTouch actually does (simple explanation)24:00 Stage 1: Survival and first product27:00 How they got their first 3 customers30:00 Why early customers are the hardest33:00 The moment they knew it would scale35:00 Growth tactics: communities, content, sales38:00 Scaling leadership from 3 people to 35041:00 Raising $200M and investor mindset44:00 Building a “generational company”45:30 Advice for founders: agency, resourcefulness, curiosity

On the premiere episode of Fork in the Road with Perry S. Kaufman, Perry sits down with Cassandra Toroian and Tracy Thomas, co-founders of VolleyBird, to explore how they built two businesses at the intersection of sports and entrepreneurship.What started as frustration over a 70-page pickleball rulebook evolved into a sports rules app powered by proprietary AI. At the same time, they launched a subscription box company serving passionate players of tennis, pickleball, padel, and golf. Every 60 days, customers receive curated gear, apparel, and sustainable products they will not find in big box stores.The conversation dives into:• Why necessity sparked their first product idea• How they pivoted their rules app from direct-to-consumer to a B2B API model• The realities of customer feedback as founders• Building a brand around sustainability and niche sports• Why working for yourself is both harder and more rewarding• What young entrepreneurs should understand before launching a businessCassandra and Tracy also share how they differentiate in crowded markets by focusing on sustainability, women-founded brands, and unique products, including eco-friendly tennis balls designed to reduce waste.If you are a founder navigating your own fork in the road, this episode offers a candid look at scaling, pivoting, and staying close to your customer while building something you truly believe in.