Why You Should Write Stakeholder Updates, Regularly.
A Tale of Three Founders
I invested in two founders back in 2021—both building developer tools, both brilliant technologists, but with radically different approaches to investor updates.
Lindiwe
Lindiwe (name changed) started sending me updates before I even invested. Her first email arrived after our initial coffee meeting: “I know we’re still just talking, but I wanted to share our monthly progress.” The update was basic—they hadn’t even incorporated yet—but it showed sharp thinking about their target customer, what they were building, and why.
What blew me away wasn’t the polish; it was how she handled uncertainty. Instead of hiding behind vague optimism, she laid it all out: her assumptions, her open questions, and how she planned to test them. One line stuck with me: “We think developers will pay for this feature, but we need to validate this. Next month’s update will include feedback from 20 developer interviews.”
I invested six weeks later. Since then, Lindiwe’s updates have been like clockwork. When they hit a major technical roadblock three months in, her update didn’t sugarcoat it. She broke down what went wrong, what they learned, and how they were adjusting. That level of intellectual honesty? Rare.
Fast forward: Lindiwe’s company has raised their Series A. They’re not a unicorn (yet), but they’ve built a profitable business with customers who love their product.
Mark
Now, let’s talk about Mark (name changed). Another founder in my portfolio. Brilliant engineer, stellar background, killer pitch. I backed him because his technical ability was off the charts.
His first update came two months after I wired the money. It was flashy, full of vanity metrics and graphs, but light on substance. When I asked about their core customer assumption—that dev teams would switch tools mid-project—he brushed it off with vague assurances.
Then the updates became sporadic. Only good news. No challenges, no learnings. It took me four months to figure out they were burning runway testing their product with the wrong customer segment. By the time Mark admitted they needed to pivot, the company had one month of cash left.
Nine months after my investment, Mark’s company was gone. It wasn’t a lack of talent or market opportunity that did them in. It was poor communication. Mark treated updates like a marketing channel instead of a tool for reflection and clarity.
Alice
An Angel Investor whom I know well, recently met Alice (name changed). —founder of a product he knows well in a market he understands inside out. He figured, as he knows how to make this company succeed - he didn’t need to do much assessment of the founder before committing to invest. Alice had also raised $1M pre-traction, which is no small feat. However, in the three months since they’ve been talking & negotiating, Alice hasn’t sent a single update. Not one. He has absolutely no clue as to which metrics she is using to measure progress, assuming that there even is progress! Has Alice got a new hire? who knows!
He only hears from her when she’s asking how long until the money lands. That silence? It’s deafening. For a founder who raised a hefty sum with no traction, updates should be her lifeline. They should show her team’s progress, her ability to execute, and her vision for the future. Instead, He is left wondering what’s happening behind the scenes. So much so that he seriously considering pulling out.
Alice’s story isn’t over yet. However, the lack of updates has already sown doubt. Trust isn’t built in a vacuum.
The Bottom Line
The difference between these founders wasn’t their technical abilities or even their market timing. It was their approach to processing and sharing information.
Lindiwe’s updates weren’t just emails—they were a masterclass in trust-building, accountability, and resilience. Mark’s failure to communicate consistently wasn’t just a missed opportunity; it was a red flag that signaled deeper issues. And Alice? Her silence makes me question whether she has the discipline to lead.
Investor updates aren’t just documents. They’re a window into how you think. When I read the first few updates from a potential investment, I’m not just looking at what they’ve accomplished. I’m asking myself:
Does this founder use writing as a tool for clarity?
Do they have the discipline to communicate transparently, even when things go wrong?
Are they learning and adapting based on real feedback?
If you’re reading this and you’re not writing updates yet, start today. Even if you’re bootstrapped or pre-investment, updates force you to get clear, stay accountable, and build trust. They’re not the only thing that will determine your success, but they’ll give you an edge—one you’ll wish you had started sooner.
Let’s take a step back. Shareholders—investors, friends and family, board members, and advisors—aren’t the only stakeholders who need to know what’s going on. Being a founder means impacting a diverse group of people, all of whom play a critical role in your success.
Here’s who else you need to consider:
Employees: They depend on you for direction, job security, and growth opportunities. Updates keep them aligned, motivated, and engaged.
Customers: They need to know about product changes, progress, and how you’re solving their pain points. Keeping them informed builds loyalty and trust.
Mentors: These people guide you through challenges. Regular updates keep them engaged and ready to offer timely advice.
Partners and Suppliers: They need operational transparency to ensure smooth collaboration and mutual success.
Co-Founders: Clear, frequent communication strengthens alignment and prevents misunderstandings.
Family and Personal Network: They often provide emotional support and, in some cases, financial backing. Keeping them in the loop can prevent strain and build trust.
The Broader Ecosystem (Community and Society): Updates on your impact can build goodwill, attract talent, and position your company as a leader in your industry.
Each group doesn’t need the same information, but they do need consistent communication. Tailoring your updates ensures they feel valued and engaged. This engagement matters. Informed stakeholders become your advocates and brand evangelists. They’ll problem-solve with you, rally behind your vision, and stick around for the long haul.
Being a founder is hard—there’s no way around it. By creating a supportive ecosystem of stakeholders who believe in you, you’ll build the resilience needed to weather challenges and scale effectively. As my therapist says - It all starts with simple communication.