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Switching 3 accounting tools in 2 years nearly broke his ops.

This episode is for non-technical founders choosing software that actually works.

Terrance, founder of Dash Oil, built a tech-enabled business in a traditional space by starting with riders (not software), validating 10 → 100 → 1,000+ users, and fixing ops before picking tools.

We also dive into the messy middle of tech adoption. What happens when off-the-shelf tools can’t keep up with shifting business models (B2C → B2B), why loyalty programs fail without field execution, and how to use tech to connect customers, retail partners, and internal teams to your end goal: trustworthy data and better decisions.

What you’ll learn

  • A simple validation path: 10 → 100 → 1,000+ customers
  • When “easy” tools become expensive (and how to avoid tool-hopping)
  • The hidden risks in loyalty/CRM (retailers claiming rewards for users)
  • A founder’s framework to adopt tech for outcomes, not aesthetics
  • Bridging B2C and B2B workflows without breaking your ops

Ready to scale with smarter tech decisions?

Listen now!

Support the show

🎙️ More from Adrian & Upstack Studio
Website: https://upstackstudio.com
LinkedIn: https://www.linkedin.com/in/adrianchinghc
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9 episodes