They didn’t just launch a wine brand - they created a whole new category. In this episode, Kendra Kawala shares how Maker Wines went from cold outreach to category leader.

Jim talks with Kendra Kawala, co-founder of Maker Wines, about how she turned B2B sales grit into DTC scale. From walking into wine shops cold to managing complex supply chains with 15 wineries, Kendra reveals the realities of launching a new product category — and why going B2B-first gave them an edge most DTC brands miss.

TOPICS DISCUSSED IN TODAY’S EPISODE

Why Maker Wines isn’t your typical DTC brand
The early grind of B2B-style sales
Managing logistics across 15 partner wineries
What business school got right and wrong
Choosing the right co-founder for scale
Order economics and conviction at launch
Applying B2B thinking to consumer marketing

If you’re launching something new — or want to scale smart — this is the episode you’ll come back to twice.

Resources:

Additional episodes you might enjoy:

Startup Ideas by Paul Graham (#45)

Nathan Barry: How to Bootstrap a Company to $30M in a Crowded Market (#41)

How I Met My Biz Partner and Less Learned Hitting $2M ARR (#44)

Ryan Hamilton on his Netflix special, touring with Jerry Seinfeld, & how to write a joke (#10)

How We're Validating Startup Ideas (#51)