It’s not easy to achieve success; if you’re reading this, odds are you know that. What you might not realize is that reaching your goals, as awesome as it is, can get in the way of the next step. This is how to keep going when the going gets good.
You’ve built something real; now here’s how you keep it.
There’s a pattern Ravi Venkatesan, CEO of Cantaloupe, has watched play out at companies of every size: a founder or executive gets very good at something, builds real success around it, and then — almost without noticing — stops taking the risks that created that success in the first place.
He calls it becoming a victim of your own success.
The mechanism is straightforward. When something is working, the logic for protecting it becomes overwhelming. Resources flow toward what generates revenue. New ideas get measured against the standard the existing model has set. The organization optimizes for repeating what already worked.
And then the market shifts.
Venkatesan — who built the SaaS platform behind credit card and airline reward redemptions, then ran Cantaloupe through a complete financial turnaround while launching two category-defining products — breaks the alternative down into a few key moves.
First: run most of the business on what’s proven — but not all of it.
Most of the business runs on what’s proven. Yet, a portion of the organization’s attention, energy, and resources is always placed on something that probably won’t work, measured against goals that are intentionally out of reach.
Second: make the stretch deliberate.
When you set a goal you know has only a 30 to 40 percent chance of being hit, you create a different kind of motion in the people working toward it. Urgency without panic. Creativity without chaos. Results that, even when short of the goal, consistently exceed what any realistic target would have produced.
Third: don’t isolate the exploratory work.
That work shouldn’t live in an isolated innovation department. When innovation is siloed, the rest of the organization feels it. Resentment builds. The team working on the moonshot becomes a special case. Standards get inconsistent. The work suffers.
His model is cross-functional from the start — built around whoever in the organization raises their hand and is willing to personally invest in the outcome, supported by commitment from across the teams rather than protected from them.
Here’s what that’s looked like in practice at Cantaloupe:
- An interactive point-of-sale device, built in six months by combining existing proprietary knowledge with outside partners, became the company’s top-selling product.
- A smart store — AI cameras, weight-sensitive scales, tap-and-go payment for fresh food — solved a theft problem that was making an entire product category economically unworkable.
Both required the same thing: getting past the instinct to only build what the company had always built.
That instinct has a name — the “not invented here” syndrome — one of the quieter ways strong companies limit themselves. The moment a company decides that only what it builds internally counts, it has closed off a set of possibilities that don’t disappear — they just get built by someone else.
If you’re running a business that’s doing well right now, the useful question isn’t just “how do we protect this?”, it’s “what are we not willing to try because this is working?”. That gap is usually where the next version of the business lives.
The full conversation with Ravi Venkatesan is on Success Beneath the Surface with Deborah Fell: https://successbeneaththesurface.com/e/ep125-ravi-venkatesan-on-moonshots-disruption-and-the-ai-threshold/