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These Bootstrapped Founders Are Playing the Long Game

How restraint, focus, and patience compound

Issue #287

January 5th, 2026

Quick Hits:

This week’s interviews feature two female founders who built durable pet brands the hard way — without outside capital and without shortcuts. One spent over a decade growing an outdoor dog brand rooted in Tahoe culture. The other turned a single product into a defensible platform — even after a Shark Tank deal fell apart.

First interview is with Rachel Skolnick Friedline - Owner & Founder of WilderDog

The second interview is with Shannon Ross - CEO & Founder of Springland

We covered:

  • Constraint forces clarity. Bootstrapping pushed both founders to obsess over getting one product right, delaying expansion until it earned its place and cash flow could support it.

  • Momentum doesn’t equal durability. From supply chain shocks and tariffs to post–Shark Tank pressure, both interviews surfaced how quickly growth can become dangerous without discipline.

  • Saying no is an operating skill. Whether it was resisting overexpansion, ignoring copycats, or waiting years to launch a new SKU, restraint showed up repeatedly as a core business advantage.

You’ve bootstrapped Wilderdog for more than a decade — a rare feat in today’s fundraising-driven landscape. What kept you committed to growing slowly and independently rather than pursuing outside capital?

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