ICYMI: The $875 Million Secret: What They DON'T Tell You About Selling a Startup

Author

Owen Drury
May 30, 2025 • Estimated Reading Time: 7 minutes

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This Week's Quickfire Bytes
Fuel your curiosity with this week's content
W/C 26th May 2025

NEW EPISODES
Most Construction Sales Reps Are Fake Consultants - Real Sales Strategy from Ediphi's Director

Trey Darnell, Director of Sales at Ediphi, shares why construction tech sales is completely broken, how most salespeople get it wrong, and why the industry desperately needs a new approach.

Find out why 90% of construction salespeople fail at their job, why platforms are becoming "jack of all trades, master of none" and how to sell construction tech without being another annoying vendor.

open.spotify.com/episode/1I5wtBlwfBrm3etufyMxHR


How PlanGrid was Acquired for $875m - Ralph Gootee, CTO

Ralph Gootee shares how PlanGrid became the first enterprise app on iPad, the brutal year-long acquisition process, and why pricing decisions can make or break your startup.

Find out why iPad was crucial to PlanGrid's success when even Facebook refused to build an iPad app, how having 5 co-founders worked despite conventional wisdom saying otherwise and why AI augments engineers but won't replace them anytime soon.

open.spotify.com/episode/0HdVexBb8IPJDkZoraWkBS


90% of Sales Demos Fail - Closing $1M Deals with Mutual Action Plans & Multi-Threading Secret to Accelerate Sales Cycles

We had Scotland Foss, who helped build PlanGrid before its $1B acquisition by Autodesk. Scotland shared his proven playbook for construction tech go-to-market success from his journey across multiple ventures.

Find out why product-market fit must come before hiring salespeople, how PlanGrid's freemium strategy created viral adoption on job sites and why unlimited user pricing models work better than per-seat in construction.

open.spotify.com/episode/7rtu92S2vQwSgizpZULYlo

2 FAVORITE QUOTES:

“You can't build a company to be sold. It's like impossible. Like it's like not, not, it's not even a good strategy building company to be sold. You have to, you need leverage. Leverage is all that matters in business to me, leverage.”

- Ralph Gootee on building a company solely for acquisition

“The reality is sales is not what sales used to be. It's, it's more of a consulting, right? Like it's more about the people in the process and less about the tech.”

- Trey Darnell on his modern philosophy of sales

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