Startup setback and how to move forward: lessons learned and next steps
Overview
A bootstrapped startup launched in August 2019 shut its doors in October 2020. At termination, the monthly recurring revenue stood around $9,700, but churn was a major challenge. The COVID-19 crisis exacerbated the struggles, and a combination of internal resignations and a lack of a clean handover left the team unable to sell or transfer the product easily. The broader market also introduced a competitor, and the product itself was a bit tangled and difficult to take over.
The team dynamic was lean: two founders remained, with a third pursuing a high-paying opportunity and one co-founder having left due to disbelieving in the product. Despite efforts, the product was not a simple takeover for another team, and churn remained high.
What’s next after a startup failure
If you’re in a similar position, here are practical steps to help you move forward with clarity and momentum:
1) Acknowledge and process the experience
– Reflect on what worked, what didn’t, and what you would do differently next time.
– Separate personal feelings from business decisions. It’s normal to feel stress, guilt, or pressure after a setback, especially in a tough market.
2) Reassess your goals and risk tolerance
– You’ve spent 15+ years in startups with a mix of outcomes. Identify what “success” looks like for you now (not just financially, but in terms of role, impact, learning, and lifestyle).
– Consider what level of financial risk you’re comfortable with as you explore a new path.
3) Leverage your network and seek candid feedback
– Reach out to trusted mentors, former colleagues, and peers who understand the realities of startups. Honest feedback can illuminate opportunities you might not see alone.
– If you’re in a challenging environment like a high-cost area, explore mentorship communities or founder groups where sharing experiences is encouraged.
4) Explore structured paths forward
– Return to a founder or early-stage operational role at another company where your startup experience is valued.
– Consider advisory roles or board positions to keep your skills sharp while evaluating new venture ideas.
– If you still want to pursue entrepreneurship, pursue smaller, validated experiments (minimum viable products with clear metrics) to reduce risk and build confidence.
5) Plan for your personal well-being
– Acknowledge the mental and emotional load. Stress and hesitation can become self-fulfilling if left unchecked.
– Establish routines, set realistic micro-goals, and allocate time for rest and recovery.
– Maintain a support system, whether through friends, family, or peer groups, to talk through concerns without judgment.
6) Practical next steps you can start today
– List three roles or opportunities you could pursue in the next 90 days, with concrete steps to apply or explore each.
– Identify one realistic startup idea (or a project within a larger company) that you can test in 6–8 weeks with minimal risk and clear success criteria.
– Schedule a 30-minute conversation with a former co-founder or trusted mentor to gain perspective on your next move and to validate your approach.
If you’ve faced a similar setback and managed to regroup, your story can offer valuable guidance. Sharing concrete experiences, the decisions you made, and the outcomes can help others while reinforcing your own approach to moving forward.
If you’d like, share a brief outline of your strengths, interests, and the kind of roles or ventures you’re considering, and I can help tailor a personalized plan or generate ideas aligned with your background.
