Failed ventures

Dear Subscribers,

I hope this message finds you well. As many of you know, the journey of an entrepreneur is rarely linear. It's an exhilarating roller coaster of highs, lows, wins, losses, lessons, and growth. Today, I come to you with a question that will help shape the future of my next ventures.

The Backstory

For context, as many of you are aware, I have been privileged to found and lead multiple deep-tech companies over the years. Some have been successful exits, while others, despite my best intentions and hard work, didn’t deliver the returns I had anticipated.

I’m always on the brink of starting a new company. But there's a crucial decision I need to make, and I'd love to get your perspective.

The Dilemma

Should I grant shares in the new company to old investors who, in our past ventures, didn't see the returns they were expecting?

On one hand, it's a gesture of goodwill. It shows we value long-term relationships, and we’re committed to making things right. It can strengthen the bond of trust and highlight our commitment to their long-term success, not just our own.

On the other hand, a new company is a fresh start. The slate is clean. Should we solely look forward and prioritize new investors and opportunities? Additionally, there are complexities to consider: dilution of shares, setting precedents for future ventures, and potentially setting a standard of compensation for past shortcomings.

Your Valued Opinion

Here's where you come in. I've always valued the collective wisdom of community input. So, I'd like to hear from you:

  1. Grant Shares: Do you believe that offering shares to old investors is a worthy gesture, recognizing our shared history and expressing confidence in the future?

  2. Fresh Start: Or do you feel that a new venture should begin on an entirely new footing, with separate considerations and opportunities for everyone?

  3. A Middle Path: Perhaps there's a middle ground, like offering old investors a first look or special terms without necessarily granting free shares.

How to Share Your Thoughts

  • Reply Directly: Respond to this email with your insights, thoughts, and suggestions.

  • Anonymous Survey: If you’d prefer to share your thoughts anonymously, click here to access a brief survey.

To wrap things up, your feedback is invaluable. Whether you're an investor, a fellow entrepreneur, a tech enthusiast, or someone who's been a long-time subscriber, your insights will be instrumental in helping shape the next steps of our journey together.

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Michael Kapoustin3 years ago

Hey Will,

I have shared the same problem. More than once in my life. And even now we are forced to pivot after losing 2 major clients. The out with the old in with the new is probably best if the business model is just failing to get any traction. Why ride a dying horse? No amount of goodwill will solve an intrinsically bad deal. If on the other hand, as is the case in our current startup, the problem is cashflow - great idea, got traction, but the revenue can't cover the operations or R and D, then for sure go back to get more money until you get through this patch. But if its just not working, then putting more money in and diluting equity is just a bad idea. Alternatively pivot! Pick what works, deprecate what doesn't. Show investors you know the problem and see the path out. Keep the same players who understand the deal. Bottom line its just not that simple. Your options did not lay out the deal. The choice should be based on the facts of the deal. Not sure I helped - Michael K.