Turning Startup Challenges into Triumphs
When you’re starting a new company, chaos is more than just a possibility. It’s practically an inevitability. Startups are truly a rollercoaster and in a startup environment, everything can change in an instant. You might wake up one morning thinking your company is doing well and go to bed in the middle of a full-blown crisis. This is something I’ve seen more than once — both earlier in my career and now as a VC at WestWave Capital.
But it’s possible for a struggling startup to come back from the edge. I would know, because I’ve seen it happen firsthand.
A startup on the verge of disaster
My journey within a company in crisis began with an invitation to a board meeting for one of our portfolio companies. I remember walking into the room alongside Bunny, our experienced managing partner, and a board member from another firm. What we were expecting was a routine overview of sales, marketing, and financial metrics. What we got was far from routine. You can imagine our shock when the head of sales began to hit us with bad news: a key customer had dropped out, the company was struggling to find customers, and prospects were stuck in the sales pipeline and not moving forward. According to the company’s financial forecast, they would be running out of cash within three months. There was none of the usual optimism startups are known for. It had been replaced by a sense of dread.
The board members and I started asking questions, trying to unearth the root causes of these issues. Why were they having so much customer churn? Was it an issue with the product itself, or had the situation changed on the customers’ side? As we dug deeper, the atmosphere grew even more charged. The founder, a distinguished scientist, sounded like he was on the verge of tears. His face was lined with exhaustion, and I could practically feel the stress radiating from him as he described his startup journey in a somber, heavy tone. He hadn’t drawn a salary for two years, sacrificing his own wealth — and many nights of sleep — to keep this venture going. His story was reminiscent of so many of the narratives in Ben Horowitz’s revealing book, The Hard Thing About Hard Things.
It was a reminder of the brutal reality of entrepreneurship. As a founder, there are moments that leave you feeling completely alone, desperately looking for the support and guidance you need to continue your startup dream. But these moments of hardship can also pave the way for growth. I’ve witnessed this personally, working side-by-side with successful CEOs, sales leaders, and marketing leaders. I was determined to help turn things around — and so were my fellow VCs.
Staging a strategic turnaround
Listening to this founder’s story of resilience and motivation strengthened our resolve. Our focus was clear: This startup was in desperate need of strategic guidance. They also needed help building a top-class sales team to revitalize their pipeline, bring in new prospects, and reevaluate their broader strategy. Our hope was that with the right guidance, we could help steer them away from the brink — and save them from the fate that awaits so many fledgling companies in the cutthroat startup world.
We went into problem-solving mode, identifying what steps we would need to take. These included:
- Bringing in VCs who believed in the same mission to generate more funding
- Leveraging our network to find key talent with experience leading sales at early stage startups
- Validating the startup’s product-market fit to build a healthy pipeline of ideal customers
Together, we collaborated on a revamped strategy and rejuvenated the sales team. In time, backed by new resources and a new game plan, the startup not only secured its seed funding but also charted a robust path toward its Series A milestone. A couple of months later, I remember opening my inbox to find an invite to the next board meeting, along with a slide deck announcing new investors and a revitalized leadership team.
Key takeaways: Lessons from a startup’s revival
What can we learn from this story?
I think it’s important for founders to understand that challenges and setbacks like these are a natural part of starting a company. They can test your patience, resilience, and dedication, but they can also pave the way to new perspectives and ways of doing business. With each speed bump you get past, you’re learning and refining your strategy. I won’t tell you to embrace those hardships, but I would encourage you to stay strong when they happen (and they will). Each rough patch is just another chapter in your startup journey, and believe me when I say, you’re not alone.
This brings me to my other piece of advice: Don’t be afraid to ask for help. Founding a startup can be isolating, but asking for guidance isn’t just allowed; it’s often the smartest move you can make. Sometimes it takes a fresh set of eyes to see the gaps in your strategy and identify the path to closing them. At WestWave Capital, we’re experienced operators who have seen the good, the bad, and the ugly of starting a company. We take pride in having our founders’ backs, especially during those extremely difficult moments, and success stories like these are one of the reasons why.
