When to Give Up

The Startup Help Desk

In this episode we talk about giving up. Startup companies are hard, and at some point you need to ask whether it's worth grinding or just moving onto something new. When do you stay the course, and when do you give up? We are here to help! In this episode we answer questions including:

• Should you keep pursuing a goal that is out of reach?
• How long should you keep trying if the business is flat?
• What happens when co-founders can't work together anymore?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!
Your hosts:

• Sean Byrnes: General Partner, Near Horizon www.nearhorizon.vc
• Ash Rust: Managing Partner, Sterling Road www.sterlingroad.com
• Nic Meliones: CEO, Navi www.heynavi.com

Reminder: this is not legal advice or investment advice.
Q1. Should you keep pursuing a goal that is out of reach?
We shared varied perspectives on this one!
Goals are meant to guide progress. Sometimes it is necessary to adjust them to stay relevant and motivating. Adjusting a goal can ensure that you keep your team’s focus on achievable and impactful results, rather than unattainable targets that may demotivate your team.
However, is is important to not create a culture where you habitually lower goals. This can incentivize the wrong behaviors. People will realize that it takes less effort to campaign to reduce the target when compared to the amount of work it takes to reach the goal. Thus, there are plenty of reasons to leave an ambitious goal unchanged – there are benefits to falling short of a goal.
If you fall short of a goal, conduct a retrospective on what went wrong and implement changes to avoid repeating the same mistakes.
Q2. How long should you keep trying if the business is flat?
Deciding to give up on your startup is a personal and often emotional choice, but there are key signals to consider:
- Team members or co-founders are leaving.
- Customers are disengaged and growth has plateaued.
- You feel increasing opportunity costs for staying with the venture.
- The company is running out of cash without a clear path to sustainability.
- There are no viable options to sell the business.
Founders often face the question of whether to persevere or pivot. While icons of persistence may inspire founders to keep going, not all startups are destined to succeed. If critical signals point to insurmountable challenges, it may be time to move on and apply lessons learned to the next venture.

Q3. What happens when co-founders can't work together anymore?
Disagreements or misalignment with a co-founder can harm the company’s growth and morale. Before making the decisions to separate, attempt to address the root causes of conflict and realign expectations.
However, if the relationship has been toxic for an extended period of time and is unresolvable, parting ways may be the best choice for your company’s future. We are not attorneys and this is not legal advice, so please consult your attorneys when parting ways with your co-founder. Ensure the separation process is clean and legal to avoid future disputes. A parting co-founder that retains large amounts of equity or board rights could impede the company’s long-term success, so consult with legal experts to protect the business.