Ep 81- How to Ace Due Diligence: Insights From a Top Angel Investor, With Tony Shipley

Invisible InkOct 19, 20251h 9min

Tony Shipley, a seasoned angel investor and former enterprise software executive, breaks down the critical elements of due diligence that separate successful investments from costly mistakes. Drawing from his experience scaling a 400-person global software company, Shipley offers a practitioner's perspective on evaluating startups' go-to-market strategies and operational foundations.

Key takeaways

•Diversify your sales channels early—relying on direct sales alone limits your ability to scale globally across diverse markets.
•Build distribution partnerships strategically when entering international markets where direct sales teams aren't feasible.
•Scale your go-to-market approach based on company size and geographic reach rather than sticking to a single sales model.

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Invisible Ink

Business Mechanics

We had every sales channel. We had direct sales. We had OEM distributors. We had channel distributors. We sold into 100 countries around the globe. So we couldn't have direct sales in all these countries. We were a 400 person company. So we had to think about how do we go to market?

Concrete example of go-to-market complexity with specific numbers (100 countries, 400 people, multiple channels). Shows the practical considerations for scaling sales operations that founders need to think through when presenting their GTM strategy.

39:18 - 39:4325s

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