Can a leopard change its spots?

TIA Ventures
3 min readFeb 15, 2021

The CEO/founder has run a small and profitable business for years. She has now decided to take VC funding to scale her business. But the pivotal question for both founder and investor is: Can a leopard change its spots?

Imagine this: a founder/CEO has, over a number of years, built and run a small, growing, and profitable business. She has produced a software product that her customers love and decides it’s time to try to grow faster. She connects with some VCs, who see that the customers love the product and despite being in business for a long time, no one has entered the market. The total addressable market is quite large and relatively untapped, ripe for large-scale penetration.

The VCs and the founder agree to a deal, and the VCs infuse capital into the business and stand back. With a well-established product that customers love, and a CEO who has proven over years that she can build and sell that product to customers, what could possibly go wrong?

The answer is: a lot.

There are real challenges with this type of ‘opportunity’, for both the founder and the VCs. And while this type of situation may indeed be a real opportunity for both parties, before proceeding we’d recommend a deep diligence dive to address the following questions.

1) Can a founder who has operated his/her business in a measured, controlled growth mode for years, and has deeply ingrained habits and practices, make adjustments/changes in the way they operate, hire, market, and sell that will enable them to scale their business? Remember this is a business that has likely employed a different caliber of talent than scaling requires. And, remember that the sales/marketing effort required in a slowly growing business with a relatively small number of customers is profoundly different than a business designed to scale.

2) Is the founder/CEO, regardless of how well-meaning and well-intended they are, psychologically capable of moving from operating in an essentially risk-minimizing ‘safe+slow’ mode, to a mode which makes bigger bets, takes bigger gambles on talent, and tolerates bigger risks on marketing/sales initiatives, etc.?

3) And finally, does the founder/CEO have an ego which is capable of embracing new talent who may be more experienced and sophisticated than they are? Talent that may challenge existing beliefs and operating modes that have served the founder well during the life of the company.

So in the interest of avoiding pain on both sides, before doing the kind of deal described above, we would:

A) Urge our fellow VCs to measure twice/cut once relative to diligencing the questions above.


B) For successful founder/CEOs of companies that fit the description above, we would suggest that you think hard about these three questions, reflect on whether you can or want to ‘change your spots’ and play a different game, and take a beat, before saying, “Show me the money!”

-Andy Greenfield, TIA Ventures



TIA Ventures

TIA Ventures is a seed-stage venture capital fund that partners with companies building emotional and visceral connections with their consumers.