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Moving Forward After Your First Startup Fails

You made the hard decision to shut things down. What next?

Kathryn O'Day
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October 14, 2025

You made the hard decision to shut things down.

It’s a rollercoaster of emotions.

But as an ambitious, optimistic person — I know you are because you started a company! — you naturally want to take action and move forward.

I’ve talked to many founders before, during, and after this transition, including ones who launched fantastic companies on the second go-round.

Here’s 6 things to help you get through it and get ready for (hopefully🤞) the next startup.


1. Mourn (But Not Too Much)

Closing a chapter, even when it’s the right thing, is hard.

You put your heart and soul into something and it didn’t work out how you hoped.

Take time to process that, explore your feelings, and come to terms with the experience.

If you skip this step, you run the risk of a “rebound” company or life decision.

I say mourn, not wallow. Don’t pretend it was nothing, but don’t let yourself sink into despair.

First of all, you did something brave and hard and risky. That’s amazing and most people will never do that.

Also, that first company is setting you up for whatever’s next. The lessons learned will be carried forward into something even better.

If you’re having a hard time, here are some things to focus on:

  • Exercise

  • Sleep

  • Healthy food

  • Human connection

  • Outdoors

  • Helping others

  • Therapy/coaching

  • BEING A BADASS WHO IS RESILIENT AND HAS MORE GREAT THINGS AHEAD!


2. To Be or Not To Be (A Founder Again)

What do marathon runners and founders have in common?

They have one of two visceral reactions when crossing the finish line:

  • I’m never doing that again

  • I’m definitely doing that again

Sometimes it can take a bit of time to decompress, but I rarely hear someone in the middle.

It’s a no or a hell yes.

You catch the founder bug — or you are glad you tried but happy to be done.

If you caught the founder bug, congratulations! Keep reading.

If you didn’t catch the founder bug, congratulations! Keep reading. (A few things won’t apply, but most will.)

What a lucky day for all blog readers!


3. Check Your Account Balance

Real talk.

How are your finances?

I know founders who poured their savings into their company, didn’t take a paycheck, have a family, or all of the above.

Sometimes, you just need a steady stream of income for a while:

  • Rebuild the savings account

  • Pay off debt

  • Enjoy some financial stability, health insurance, and overpriced coffee drinks

If you know you want to found again but need a “regular” job, what role or company would help you develop skills for your next company?

Founders are often strategic about this.

They get enterprise sales jobs, explore new industries, or work for amazing leaders — with a plan to take those learnings into the next business!


4. The Not-While-Building Bucket List

What are the things you wanted to do in the middle of startup chaos but couldn’t?

Do those now!

They don’t have to be wild and crazy. It might be as simple as:

  • Read a book

  • Meet a friend for brunch

  • Volunteer at your child’s school/team

  • Mid-day nap

  • Visit your parents

  • Anniversary trip

  • Anything else you wanted to do when “I have more time”

These are a gift to yourself and your loved ones and will help you recharge!

Get it in now…before you start your second company 😉


5. Never Let a Good Crisis Go To Waste

The post-mortem, good and bad, is key!

  • What went well?

  • What didn’t work?

  • What do you want to do differently next time?

  • How will you ensure you do it differently? What is going to change?

  • When were you having the most fun?

  • What are areas of weakness? How can you improve or mitigate those?

Most founders have already obsessed and agonized over what went wrong.

Here’s how to make it productive and action-oriented:

  • Write it down. Putting it into words forces clarity.

  • Set goals for the next business. e.g. I will do at least 100 conversations before building anything. If I don’t have $100k in revenue within a year, I’ll find a different idea. Put these in a calendar reminder for the future!

  • Look in the mirror. If it’s all your evil co-founder’s fault, you haven’t done the work. An evil co-founder was chosen and enabled by you in some way. Understand your patterns so you don’t repeat them.

  • Get an outside opinion. Talk to trusted advisors and ask about their takeaways for the business and your performance as a founder.


6. Explore What’s Next

Last but definitely not least…

Start laying the breadcrumbs for your next endeavor:

  • Build relationships with people you like and respect

  • Find interesting topics and dig in

  • Run tests, research markets, try out new technologies

  • Do things that are fun, energizing, and fulfilling

I had a founder use the phrase, “Follow the stepping stones.”

She wasn’t forcing an idea or a process but rather naturally moving to the next question, meeting, or topic.

You never know who you will meet, what will spark an idea, or where the next business will come from!


If you’ve gone through this process, what helped you? What do you recommend to other founders?

P.S. If you’re exploring and want inspiration, A.T. Gimbel wrote a great post about markets in need of disruption and we’re always brainstorming ideas and markets in our Venture Studio!

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