Dear hustlers, founders, operators and visionaries,

Pivots, exits, and finding the right pace – the journey of a founder is anything but linear. Sometimes, success means knowing when to let go, when to change direction, and when to take a step back to reset.

In this episode, we sit down with Jessica Holzbach, serial entrepreneur and co-founder of Penta and Pile, to discuss the realities of pivoting a startup, navigating acquisitions, and staying sane while building ambitious companies. Jessica shares candid insights on managing high-stakes decisions, balancing long-term vision with financial realities, and redefining success beyond just scaling fast.

Exclusively for our newsletter subscribers, Jessica has shared additional insights below.

🎧 Tune in now on Spotify or Apple, and share your thoughts! Who should be our next guest?

In the meantime: Follow the Gradient and stay tuned!

🫶🏼 Melanie & Christian

PS: Has this e-mail been forwarded to you? Sign up here.

Pivoting, exiting & starting again

What you will get out of this episode

In our conversation, Jessica shares:

• The art of the pivot: How to recognize when your startup needs a strategic shift and how to navigate it effectively.

• Hard truths about traction: Identifying real demand vs. wishful thinking when launching a product.

• The psychology of exits: What it really feels like to sell your company and why the emotional aftermath can be disorienting.

• Managing team transitions during change: How to communicate a pivot or exit effectively while keeping trust and morale intact.

• Balancing ambition with personal well-being: Lessons learned from running at full speed, taking breaks, and finding a sustainable work rhythm.

Our main take away’s

1. Pivots require brutal honesty: If traction fades or customers hesitate to pay, it’s a signal to reevaluate. Jessica shares why she ran two parallel teams – one testing a new model while the other pushed to validate the existing one – to ensure the right decision.

2. Charge from day one: Free users don’t always convert to paying customers. Jessica learned the hard way that validating willingness to pay early on creates a more sustainable business.

3. Exits are complex – beyond the deal itself: Selling your company isn’t just a financial transaction – it’s an emotional one. Founders should prepare not just the business but also themselves and their teams for the transition.

4. Energy management is key to long-term success: After multiple startup journeys, Jessica is now focused on finding a pace that’s both productive and sustainable – avoiding the cycle of intense sprints followed by energy lows.

5. Time off matters: Sailing, disconnecting from work, and reflecting without distractions have helped Jessica reset between ventures. She emphasizes the importance of defining what a great life looks like – and making choices accordingly.

Additional material on the topic

• Lovable is the tool, Jessica named in the conversation to quickly test hypothesis.

• Jessica has a column at Gründerszene and wrote a really insightful article [in German] about how to do a pivot.

• ‘What do I do with my money, and with my life?’ The club helping founders deal with post-exit blues

How to reach out to Jessica

• Jessica on LinkedIn

Exclusive from Jessica

Are there any books, podcasts, or frameworks that have helped and inspired you throughout your journey so far?

I love books, some are: Four steps to epiphany (for finding PMF), The great CEO within (Leadership), Trillion Dollar Coach (Leadership), The Power Law (Venture Capital)

If a founder is being approached for an acquisition, what are the top three questions they should ask potential buyers to ensure alignment?

1. What is the single most valuable asset you are buying? (Find out wether it is for team, customer, market expansion etc etc) Really dig into the REAL motivation

2. Have you managed M&A transactions before and how do you plan to integrate the companies?

3. If all goes right, what can we achieve together?

How do you keep your team motivated and secure during the uncertainty of an acquisition process?

Over- communicate, be deliberate and plan your communication and massages very well and repeat them as often as possible

What’s one red flag you’ve experienced - or seen - that founders should watch for during acquisition negotiations?

It's a process based on trust, for both sides. Do not burn this relationship by lying to make things look better - especially after an acquisition is through you will have to disclose everything anyways and if the acquisition is structured well, you will bear the consequences.