Pivoting, Exiting & Starting Over – Hard Truths from Jessica Holzbach

For many founders, an exit is the ultimate goal. But what happens after the deal is done? Is it the finish line—or just the start of a whole new challenge?

Jessica Holzbach knows this firsthand. She’s a serial fintech founder and angel investor who co-founded Penta, scaled it to 35,000 SMEs, and later exited both Penta and her second venture, Pile.

In this episode, we dive deep into three critical moments in every founder’s journey:

• Pivots: When do you know it’s time to change direction? And how do you pivot without losing your team?
• Exits: What founders often overlook, the emotional rollercoaster, and why selling your company isn’t always the fairy tale it seems.
• Starting Again: The single most important question to ask before launching your next venture.

If you’re a founder, operator, or thinking about what’s next, this conversation is packed with insights you don’t want to miss.

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