On Episode 13 of Sideways Rain, JR and Kris sit down for a raw, reflective, and at times surprising look back at the two-year journey of building WIFT—from a casual birthday-day LinkedIn message to beta pilots, tough pivots, missed timelines, surprise wins, and the resilience it takes to keep going.
They talk about what sparked the idea, the decision to go with a barber-recommended developer (yes, really), the highs of IMEX 2024, the sting of rejection from a major player, and why humility, patience, and persistence matter more than any pitch deck.
This one’s for anyone who's ever tried to build something from scratch—and kept going even when the shine wore off.
Topics covered:
How WIFT started (and why it wasn’t supposed to be a tech company)
Choosing the right partners (and what makes someone trustworthy)
MVP missteps and how much it really costs
The power of listening to your market
Learning to celebrate wins—without getting too comfortable
