Benefits of Frequent Investor Updates

10 Years. 120 Monthly Updates. Zero Missed. I sent my first investor update for Blue J in early 2016. As of this month, we’re closing in on 120 consecutive updates. I’ve never missed one. Many founders treat investor updates as an administrative chore. That’s a mistake. A monthly update is one of the highest-leverage tools a CEO has. Here’s why. 1️⃣ It forces you to work on the business, not just in it. Once a month, you have to step back, prioritize, and explain trajectory instead of tasks. You can’t hide in tactics when a summary is due. 2️⃣ It saves you time. Counterintuitive but true. When people know a clear update is coming on a predictable cadence, the random “just checking in” messages stop. 3️⃣ It signals executive reliability. Consistency signals organization, conscientiousness, and control. If you can’t reliably communicate in calm times, investors will doubt you in a crisis. 4️⃣ It builds trust equity. Don’t hide. Friends, family, and angels are rooting for you. Transparency during good months earns the trust you’ll need during bad ones. 5️⃣ It creates real accountability. Writing “here’s what we said we’d do” next to “here’s what happened” every 30 days is a powerful form of self-governance. 6️⃣ It sharpens thinking. Writing is thinking. You often don’t fully understand an issue until you try to explain it simply to others. 7️⃣ It activates help. People want to help but don’t know how. A clear “Asks” section routinely unlocks unexpected support. 8️⃣ It becomes the factual history of the company. Memory lies. Monthly updates don’t. Years later, this archive shows how things actually unfolded. 9️⃣ It compounds relationships. Investors who’ve read 40 or 50 updates feel genuine ownership of the journey. Customers and candidates do too. Below are two screenshots. The first is from March 1, 2016, our very first monthly update. The second is from today. Same habit. Same cadence. Very different company. Start early. Keep it brief. Be honest. Send it on the same day every month. Never miss. Consistency compounds.

As a first-time founder, I made this post-fundraising mistake that didn’t seem like a big deal. But it was — and I really wish someone had told me to fix it. I didn’t go silent. But I wasn’t consistent with investor updates. And especially when things weren’t going great, I hesitated to hit send. I still see LOTS of founders doing the same — sending investor updates too infrequently, without a regular cadence, or going quiet during the hard stretches. The good news? It’s an easy thing to fix. And if you're not convinced, here are the top reasons why *monthly* updates are important: - No news = bad news - when investors don’t hear from you, they assume the worst. Silence creates a vacuum — and it usually fills with doubt, not optimism. - Trust builds through consistency - clear, regular communication helps build trust over time. When you share both wins and challenges, you give investors real context — and make them feel more connected to your journey. - Regular [monthly] cadence matters - startups move fast. Things can change dramatically in a few months. NFX data shows 60% of seed founders send monthly updates. Think of it this way: If you raised 18 months of runway and only send quarterly updates, your investors may only hear from you 4–5 times before your next raise. That’s not enough exposure to build a deep relationship. - Help follows communication - no one expects everything to go perfectly. And investors want to help. When you're in regular communication they understand context and you're more top of mind so they are more apt and able to help. Pro tip - make specific asks in your updates but vary them so you avoid "ask blindness" (which happens when you list the same things each month). - Memory outlasts your startup - even if your startup doesn't succeed (and most don't), investors will remember your professionalism, communication and transparency. That makes them want to work with your again and tell others the experience was positive. Shoutout to James Gordey and Jimmy Douglas for sending great, regular updates. What do you think - agree or disagree with the importance of monthly updates?

One of the simplest but most underrated ways to strengthen a founder’s relationship with investors is through regular investor updates. What Is an Investor Update? It's a concise letter from the founder that includes business performance, financial metrics, key updates, challenges, and asks. The goal is simple: build trust and keep investors engaged in your journey. Why Should Founders Send It? 1. Build Trust: Consistent, transparent communication helps investors understand how things are progressing. 2. Prepare for Future Fundraising: Regular updates make it easier when it’s time to raise again. Investors already know your trajectory, so you don’t start from zero. 3. Unlock a Bigger Resource Pool: Your investors have access to talent, capital, networks, and expertise. Sharing your challenges helps them help you. Key Principles 1. Frequency: Monthly is ideal. Quarterly can work depending on your stage. 2. Consistent Metrics: Pick the right metrics, and stick to them. Don’t shift based on performance. 3. Clear Format: A consistent update structure helps investors track your progress over time. How to Structure an Investor Update 1. Set the Stage: Investors get hundreds of emails. Start with a quick overview so they know what to expect. 2. Share Financial Metrics (with context): Revenue, ARR, GM, Contribution Margin, EBITDA, Burn, Runway, etc. Numbers matter, but the story behind the numbers matters more. 3. Add Product & User Metrics: DAU/MAU, retention, activation, acquisition, etc. Retention is especially important as it tells the truth about product quality. 4. Highlights & Lowlights: Be honest about wins and losses. Investors value transparency more than perfection. 5. Notable Updates: New hires, partnerships, product launches, strategic changes; anything that moved the needle. 6. Your Ask: Be specific about where you need help. Investor networks are powerful; learn to use them. 7. Close with Gratitude: A simple thank you goes a long way in keeping relationships warm. Regular updates aren’t just a reporting tool; they are a strategic advantage. Founders who communicate consistently build better relationships, get access to capital faster, and get more support when it matters. If you’re a founder and haven’t started sending investor updates yet, now is a good time to begin.

Monthly Investor Updates: Only 2 in 10 startups do this. I unlocked investor value by writing it for 23 months + ⏱ It takes me 1.5hrs every month ✏ I use a template to reduce cognitive overload 📃 Here is a simple structure that I use every month - key metrics (NSM, runway, etc) - 3Ps - progress, problems, plan Here is the magic that happened: 1. || Builds discipline || This is the same concept of building any habit James Clear in the book Atomic Habits teaches you what and how (10/10 recommend reading). 2. || Gives space to zoom out || While writing the update, I once ran a new sub-metric on activating signups and was surprised at how successful we had been! Founders live in the daily micro of things. zoom-out is needed. 3. || Builds a deeper investor relationship || One investor once said to us: “founders often go dark. It’s amazing you guys send updates every month. I know you are going to make it” 4. || Share bad news real time || The discipline of monthly updates stops a founder from overthinking the investor reactions to bad things. I have shared legal issues, employee changes, whole product model changing (4 times!), high burn etc. The responses were always way better than what we imagined. Stop fearing the unknown. 5. || Allows investors to add value || I've received help on growth hacks, SEO help, intro to celebrities, offers for investing in Series A, unadulterated customer feedback, worries re our pivots, and more. There is SO MUCH knowledge within your investors. Unlock it 6. || Sharpens data analysis & storytelling || I look at metrics important to us, and any data on our progress (+ve or -ve). In the 2023 recap, I mentioned 3 pieces f*** ups + and calculated a rough monetary value - Tech/ QA errors: £100-150k, UX issues: £70-100k, Google Ads: £50-70k. This analysis gave me a new data point and helped me articulate the tough lessons. That improved my storytelling. 7. || Holds you accountable || I love the last 2Ps (progress, plan). I never want to repeat the same problem, and want to deliver on the plan. If I don't, I revisit, iterate and improve. 8. || Allows you to run tests || One month, we had I had an assumption "do investors track our monthly metrics or want an overview", We ran a test. We didn't send the Dec number, but sent the 2023 recap instead. NO investor came back. We didn't care either way, but it was fun to fail our test! 9. || Increase your rate of learning || Because of #2, #6, #7, #8, you end up learning a lot faster! What a bloody exciting side effect. It's addictive. 10. || Communication style || When I started the updates, my tone was defensive and I rambled. Over time, I've become ruthless with being as unbiased (as possible) and become concise. This has allowed us to unlock more value. Thank you to our AMAZING investors 💗 I love #1, #2, #3. What about you? #founders #startups #tech #vc #investors #investorupdates #angelinvestor #entrepreneurship #productinnovation

One of the most overlooked factors in a startup’s success? Consistently sending investor updates. From my experience as an entrepreneur and angel investor, there’s a strong correlation between companies that send regular updates and those that succeed. It’s not a perfect rule, but there’s definitely a relationship. When I started Rewind, I made it a top priority to send regular updates—not just to our current investors, but to potential investors as well. Doing this early on had three big benefits: 1️⃣ Fresh perspective on the business. Stepping back each month to write updates forced me to look beyond the day-to-day. I could focus on trends and the bigger picture. 2️⃣ Deeper accountability. Writing updates made me understand every aspect of the business more thoroughly. I had to be fully accountable for the numbers, milestones, and challenges I was reporting. 3️⃣ Saved time with potential investors. When I met with investors, they already knew how Rewind was doing. We could skip the basic updates and dive right into more strategic conversations. I’ve kept up this habit for over 10 years. In the coming weeks, I’ll be sharing more on exactly how I do it—including practical tips for early-stage entrepreneurs. Follow me if you want to learn the specifics and start building better relationships with your investors.

Q1 just ended. Time to write that investor update. I know—you’re busy. Building, selling, hiring, putting out fires. Writing updates feels like just another task on the list. But here’s the thing: • They build trust. Even when things aren’t perfect (they rarely are), regular updates keep investors engaged. • They create opportunities. Investors talk to hundreds of people every month—your update keeps you top of mind for intros, advice, or funding. • They bring clarity. Summarizing forces you to step back and focus on what truly matters. Keep it simple: ✅ Key metrics (the ones that count) ✅ Wins & challenges (be real) ✅ How we can help (specific asks work best) ✅ Burn & runway (yes, we need to know) The best founders do this consistently, good quarter or bad. It’s not about impressing—it’s about building the habit of clear communication. Bonus tip: Take a moment to publicly thank those 2-3 investors who really helped this quarter. Competitive dynamics work in unexpected ways. Take an hour, write it, hit send. Your investors will notice.

Hot take: Monthly investor updates are better than quarterly ones. Whether it’s a startup or a business you have acquired, your investors want to know what’s going on. Sending out regular, detailed updates is one of the best habits I've built as an operator. Why monthly matters: 1) It forces discipline. If I cannot explain performance, pipeline, and risks, I do not know the business well enough. 2) It builds trust. Whether the news is good or bad, steady communication shows you are on top of it. 3) It creates a record. Twelve consecutive updates tell the story of how value was built throughout the year. What to include: 📌 Financials: revenue, EBITDA, volume, cash 📌 Pipeline: customers, contracts, or acquisition targets 📌 What happened: key wins, losses, lessons learned 📌 Team: hiring and leadership changes 📌 Risks: operational issues and what is ahead 📌 Market: industry, policy, or regulatory shifts 📌 Focus: priorities for next month or quarter 📌 Culture: the fun stuff that shows who you are 📌 Ask: how investors can help How to do it: 1) Be consistent - same day every month. I send mine on the 15th, so I can include last month’s financials. 2) Be efficient. Consider writing in the "Smart Brevity" style, so key points and numbers are easily scannable. 3) Be real. Your updates shouldn't be mundane or repetitive...let your personality and enthusiasm for the business shine through! Some may think monthly is too much, but most appreciate being informed and engaged. Send it!

I have read investor updates of multi-billion dollar companies, written investor updates for 9 figure companies, and now I'm beginning to write them (with the help of Will!) for our startup. This is a practice that is valuable for companies of ALL sizes, so I wanted to share some perspective on why it matters: 1/ It clarifies your own thinking. Good writing = good thinking, period. Yet busy founders rarely take the time to truly stop & think. It can subconsciously feel like a luxury, or a waste of time. But the biggest waste of time is running hard in the wrong direction. Carving out dedicated time each month to A) reflect on where you've been / where you're going and B) communicate that clearly to others is invaluable. 2/ It creates external AND internal accountability. By writing out your goals & views of the future, literally signing your name on it, and sending it to people you deeply respect (hopefully, if you have good investors..), you create MASSIVE accountability for yourself. Our investors don't ever have to ask me about what I've written. The simple fact that I know I have claimed some goal and have shared it in writing makes me want to do everything I can to achieve it. It allows investors to keep me accountable, and it also helps me to keep myself honest. 3/ It allows you to leverage the brainpower & connections of your investors. Our investors are smart, experienced, and well-connected. We want them to be in the loop. We want to constantly be uploading context to their brains so they can weigh in on tough decisions if we need them. Or pull from their own experience to make recommendations. Or make valuable introductions for us. Not being in the day-to-day, they're also more objective about our business than we can ever be. Bottom-line: all founders should write investor updates. I'd go so far to say that even if you HAVEN'T raised funds, you should be doing this. The clarifying value of the process is invaluable.

Founders send updates monthly, quarterly, or at least somewhat regularly. And when you don’t? Everyone assumes something is wrong. If you never ask for anything, investors usually won’t do anything. If you need help, we probably won’t know. And when you finally reappear, we have to spend time catching up on what should’ve been obvious all along. The truth is simple: you have to tell us what’s going on. When you do, people will reach out, follow up, advocate, share your news, and stay engaged. When you don’t, they won’t. Silence isn’t neutral. It erodes support. The other side of updates is just as important. Regular reporting forces you to benchmark your own execution. Track your product, revenue, team, pipeline, burn, whatever matters to your business. Good operators measure everything. Great operators turn it into a habit. And if you’re already doing it for yourself, sending the update to your investors is almost zero extra work. But the impact compounds. It builds trust, unlocks help, and keeps momentum moving forward. If you want your investors to show up for you, you have to show up for them first.

One of the most underrated growth levers in a drinks business isn’t distribution, packaging, or pricing. 𝗜𝘁’𝘀 𝗵𝗼𝘄 𝘆𝗼𝘂 𝗰𝗼𝗺𝗺𝘂𝗻𝗶𝗰𝗮𝘁𝗲 𝘄𝗶𝘁𝗵 𝘆𝗼𝘂𝗿 𝗶𝗻𝘃𝗲𝘀𝘁𝗼𝗿𝘀. In my conversation with Jen Pelka, co-founder and CEO of Une Femme Wines, she shared something that resonated: The single most impactful change they made in fundraising wasn’t a deck tweak or a new story — it was committing to a monthly investor update. Not quarterly. Not “when things are good.” Monthly. Every time. Here’s why that mattered. As Une Femme scaled — from early days to a ~300K-case national brand — capital needs didn’t go away. If anything, they became more complex. Production cycles, national accounts, inventory timing, format shifts. This is a capital-intensive business, even when things are going well. Instead of treating investors as people you only call when you need money, Jen and her team treated them like long-term partners. 🔶 𝗠𝗼𝗻𝘁𝗵𝗹𝘆 𝘂𝗽𝗱𝗮𝘁𝗲𝘀 𝘁𝗵𝗮𝘁 𝘄𝗲𝗿𝗲 𝗵𝗼𝗻𝗲𝘀𝘁 — 𝗻𝗼𝘁 𝗷𝘂𝘀𝘁 𝗵𝗶𝗴𝗵𝗹𝗶𝗴𝗵𝘁𝘀 They didn’t sugarcoat hard moments. When the industry slowed, when headwinds appeared, when things didn’t go to plan, investors heard about it in real time. 🔶 𝗖𝗹𝗲𝗮𝗿 𝗮𝗿𝘁𝗶𝗰𝘂𝗹𝗮𝘁𝗶𝗼𝗻 𝗼𝗳 𝘄𝗵𝗮𝘁 𝘁𝗵𝗲 𝘁𝗲𝗮𝗺 𝘄𝗮𝘀 𝗹𝗲𝗮𝗿𝗻𝗶𝗻𝗴 Each update forced internal reflection: What worked, what didn’t, and what they were adjusting. That discipline sharpened decision-making inside the company — not just externally. 🔶 𝗔 𝘀𝘁𝗲𝗮𝗱𝘆 𝗱𝗿𝘂𝗺𝗯𝗲𝗮𝘁 𝗼𝗳 𝘁𝗿𝘂𝘀𝘁 Nothing came as a surprise. By the time Une Femme raised again, investors already understood the business, the risks, and the strategy. The outcome surprised even them. Those updates didn’t just keep investors informed — they changed how investors showed up. Many reinvested. Many made introductions. Some became active advocates, not because they were asked to, but because they felt included in the journey. That’s the real lesson here for founders. 𝗖𝗮𝗽𝗶𝘁𝗮𝗹 𝗶𝘀𝗻’𝘁 𝗷𝘂𝘀𝘁 𝗺𝗼𝗻𝗲𝘆. 𝗜𝘁’𝘀 𝗿𝗲𝗹𝗮𝘁𝗶𝗼𝗻𝘀𝗵𝗶𝗽𝘀, 𝗽𝗮𝘁𝘁𝗲𝗿𝗻 𝗿𝗲𝗰𝗼𝗴𝗻𝗶𝘁𝗶𝗼𝗻, 𝗮𝗻𝗱 𝗮𝗰𝗰𝗲𝘀𝘀. And how you communicate can determine whether investors behave like a checkbook — or like an extension of your growth team. For drinks founders navigating today’s tougher capital environment, this is one of the most practical tactics I’ve heard. We dig deeper into this — along with scale, format strategy, and national account growth — in the full Business of Drinks episode with Jen Pelka. 👇 #BusinessOfDrinks #FounderAdvice #InvestorRelations #DrinksIndustry #BeverageFounders #StartupLeadership #ScalingBrands Scott Rosenbaum Caroline Lamb