Is it possible to turn an early-stage startup into a $200M acquisition in under two years? According to Kevin Henrikson, the answer is a resounding yes—but only if you move faster than you’re comfortable with, learn from every user interaction, and tackle big-company partnerships the right way. I recently spoke with Kevin on the No Hacks Podcast, where he shared the story of co-founding Acompli, selling it to Microsoft in just 18 months, and shaping it into Outlook Mobile—now a standard productivity tool for millions of people worldwide.
The conversation explored how Kevin discovered a passion for breaking and fixing things early on, why shipping an MVP “too late” is a wasted opportunity, and how “advisor mode” can help you thrive in a corporate environment after an acquisition. We also discussed the role of AI, focusing on how automated tools can handle tedious tasks, letting humans do the creative heavy lifting.
If you’re a founder, product manager, or anyone fascinated by the interplay of rapid execution and sustainable growth, you’ll find valuable insights from Kevin’s story.
The Early Spark for Building and Fixing
While Kevin’s background includes an unconventional starting point, what’s more important is his early realization that tinkering—and sometimes breaking things in the process—can be the best way to learn. From taking apart go-karts as a kid to the hours spent experimenting with computer code in college, he was always driven by a deep sense of curiosity.
That willingness to dive in and get your hands dirty became a crucial advantage in his startup journey. Instead of overthinking or waiting for perfect conditions, Kevin embraced the mindset of “try, fail, learn, repeat.” And it paid off big time when he eventually decided to tackle the mobile email experience, which had long been clunky and disjointed.
Moving Fast: The Core Philosophy
When Kevin co-founded Acompli, the primary goal was to solve a persistent problem: combining personal and enterprise email in a sleek, unified experience. At the time, solutions like Gmail and Microsoft Exchange felt like two separate worlds. On mobile, that meant multiple apps, subpar calendar integrations, and a general lack of fluidity.
Kevin and his team believed they could fix this—but only if they moved quickly. He shared a principle I’ve heard echoed among many successful founders: “If everyone loves your MVP, you shipped too late.” It’s a powerful reminder that shipping a less-than-perfect product earlier is key to gathering authentic user feedback.
The friction and imperfection you encounter with early adopters become fuel for your iteration cycle. If you launch when it’s already polished, you may have validated (and missed) entire avenues of innovation because you never saw how real users struggled or what they truly wanted.
The “Kleenex User” Concept
One particularly memorable concept from Kevin is what he calls the “Kleenex user.” Much like a Kleenex that’s only fresh the first time you pull it out of the box, a user’s very first interaction with your product is a rare, one-time event. After that first session, they’re no longer brand-new—they’ve been “used,” so to speak.
This matters because first impressions are critical. If your onboarding is confusing or if you’ve buried the product’s core value under multiple layers of UI, you’ll lose people before they ever get to the good stuff. More importantly, you’ll never have that pristine, first-time perspective again. That’s why Kevin insists on closely monitoring those initial user sessions—and reacting immediately to any friction they encounter.
From Acompli to Outlook Mobile in 18 Months
So, how does a fledgling startup secure a $200M acquisition by Microsoft in just a year and a half? Kevin’s story with Acompli proves that it’s part timing, part execution, and part being willing to integrate exactly what a big player needs.
Their goal was ambitious: build an app that does email, calendar, and file attachments more seamlessly than native apps could manage, and handle both personal Gmail accounts and enterprise Microsoft Exchange. That dual approach caught Microsoft’s eye—Acompli wasn’t just a consumer product; it was also enterprise-ready from day one.
Soon enough, a conversation started about whether Microsoft could license Acompli’s tech for its mobile email. But the deeper that discussion went, the more it became clear that acquiring Acompli outright would be the best move. The result? Acompli was absorbed into Microsoft and quickly rebranded as Outlook Mobile.
Life After Acquisition: The Advisor Mindset
Joining a tech giant is a different world compared to a lean startup. Kevin stresses the importance of becoming an “advisor” within the larger organization, rather than trying to bulldoze corporate processes. This means offering thoughtful solutions to existing challenges and understanding that big companies have complex internal structures—for better or worse.
If you charge in with a “we know best” attitude, you risk alienating the people who’ll ultimately determine whether your product thrives inside the new environment. By taking on the advisor role, you can gradually steer the culture and processes in a more agile direction, leveraging the corporation’s vast resources while preserving the innovative spirit that got you acquired in the first place.
Embracing AI for Smarter Workflows
As our conversation shifted toward the future, Kevin discussed how AI and automation are changing the nature of startup scaling. He’s especially intrigued by the concept of multi-agent AI—the idea that multiple specialized bots can handle different aspects of your workflow, from scheduling to data analysis, before handing off to a human for final decisions or creative flourishes.
For Kevin, AI isn’t about replacing people. It’s about freeing humans from repetitive tasks and giving them more time to focus on strategic, imaginative endeavors. This is a thread that’s becoming more and more prevalent across industries: harnessing machine intelligence to make teams more effective and nimble, rather than simply cutting costs.
Rapid Execution vs. Sustainability
One might wonder if Kevin’s “ship fast” mentality ever risks burning out teams or ignoring critical long-term considerations. He acknowledged that the tension between speed and sustainability is real. You can’t just brute-force your way to success by releasing chaotic products every week. However, a well-orchestrated approach—where you have clear priorities, minimal wasted effort, and a laser focus on user feedback—lets you sprint without running off a cliff.
In other words, speed is a tool, not a rule. You still have to be data-driven, iterative, and, above all, open to the idea that you’ll need to revisit certain systems or codebases once you confirm product-market fit. The difference is that you won’t be spending your precious early days polishing a feature nobody cares about.
Key Takeaways
- Ship Fast for Real Feedback
- Waiting for perfection means losing out on crucial early adopters who can show you what matters.
- Value Your “Kleenex Users”
- Protect and learn from fresh eyes; you only get one shot at a perfect first impression.
- Advisor Mode After Acquisition
- Earn trust in a big corporation by suggesting improvements, not force-feeding them.
- AI Is Your New Teammate
- Let automation handle basic tasks so humans can innovate and strategize.
Final Thoughts
Hearing Kevin’s story reminds us that success in tech often hinges on the dance between speed and thoughtful iteration. You can’t stand still—but you also can’t sprint blindly. That sweet spot is where feedback loops guide you to create a product that’s genuinely needed and loved.
Ready for more details straight from Kevin? Check out the full podcast episode: [Insert Your Podcast Link Here]. If you’re interested in scaling strategies, post-acquisition survival, or leveraging AI to supercharge your workflow, you’ll find plenty of inspiration in our chat.
Let me know your thoughts in the comments—what’s your biggest takeaway from Kevin’s rapid-execution approach, and how are you balancing speed with sustainability in your startup or project?