Lessons from a Year of Pivoting and Building

Pivoting to an AI product taught us lessons on market timing, messaging struggles, flexibility challenges, and the myth of quick MVPs.

Last year around this time, we made a bold choice. We pivoted from working on an engineering productivity tool to building an AI-powered product management platform. It wasn’t just a shift in direction; it was a complete reimagining of what we wanted to create, who we wanted to serve, and how we envisioned the future of product management.

‍If you’ve been following along, you know we like to keep things dynamic, and that philosophy extends to everything we do. Strive is now something I could only dream of a year ago: a platform that’s data-driven, flexible, and—dare I say it—completely unlike anything else out there.

‍As 2024 comes to a close, I’ve been reflecting on the lessons this wild ride has taught me. So here’s my honest take on what I’ve learned (sometimes the hard way):

‍1. You can’t control everything. Actually, you can’t control most things.

‍Markets, macroeconomic conditions, global trends—these all have a much bigger say in your success than you’d like to admit. It’s humbling and a bit frustrating, but it’s also freeing when you realize that your best move is to focus on what you can control: your product, your customers, and how you respond to change.

‍2. Timing with investors is everything.

‍In the early months, we spent way too much energy trying to attract investors. And sure, we got meetings and interest, but here’s the thing: unless the stars align (aka point #1 is in your favor), it’s a tough game to win. If I could do it over, I’d spend more time building value for our customers and let the right investors find us when the timing aligned.

‍3. Don’t buy into the ‘startup fairytales.’

‍I learned this one 15 years ago. You know those books that tell you how to ship a market-ready product in a month? Yeah, no. That’s great advice if you’re building a consumer app or something lightweight for individuals. But for a product aimed at the mid-market—even for early-stage companies—it’s a different story. The bar is higher. The value has to be clear. And for most of us solving big, complex problems, delivering something meaningful in four weeks is a fantasy.

This isn’t just theory. My last endeavor, Quality Management for Cloud Providers, taught me this firsthand. The MVP wasn’t enough. Not for customers, not for the market, and certainly not for the standards they held us to. If you’re building for the mid-market or beyond, an MVP has to be much more than a “minimum.” It has to add real value out of the gate. Hands down.

‍4. Messaging is my arch nemesis.

‍No exaggeration—messaging has been the toughest part of building Strive this year. It’s like trying to condense an entire symphony into a single chord. Just when you think it sounds OK, someone comes along, looks at what you’re building, gets it, goes absolutely crazy over how much it could save them in time and money… but then drops the bomb: “Your website is unclear. If you hadn’t reached out to explain, I wouldn’t have noticed.”

Yeah, that happened last week. It’s great that people see the value when you explain it, but it’s also a stark reminder that your messaging needs to do the heavy lifting when you’re not in the room.

I was glad to see a post some time ago from Bobby Pinero of Equals. They’ve talked a lot about their own struggles with messaging, calling it “the quest for the perfect homepage.” Their blog is a lifesaver for the self-conscious entrepreneur (hi, guilty). I love how they lay out their mistakes with such transparency—it inspired me to write this post as a bit of an homage.

What I’ve learned? Messaging isn’t about dazzling people with cleverness; it’s about connecting the dots as clearly as possible. And if you’re building something flexible and dynamic like Strive, that’s easier said than done. But narrowing your focus to solve one specific, undeniable pain point is the best way to make people stop, pay attention, and say, “I need this.” Fortunately, getting there.

‍5. Flexibility is a double-edged sword.

‍We built Strive to be flexible and dynamic, which is great for customers but a nightmare for messaging. How do you explain something that can do a lot? The answer: you don’t. You focus on one narrow pain point, solve it incredibly well, and expand from there. Easy to say, brutally hard to execute.

Flexibility also makes prioritization tricky. When your product has endless potential, the question becomes: what matters right now? For us, the answer was listening to our early beta customers, identifying the biggest pain points, and doubling down on delivering solutions for those. Flexibility is powerful, but it has to be reined in.

‍Reflecting on these lessons, I feel a mix of pride, humility, and determination. Building a product like Strive isn’t easy—nothing worth doing ever is—but it’s been one of the most rewarding experiences of my life.

‍As we step into 2025, I’m excited to see where this journey takes us. And if you’re a product manager struggling with data overload, messy workflows, or figuring out what to focus on next, I’d love to chat. We’re here to make your life easier—because we’ve been in your shoes, and we’re building Strive to solve the problems we know all too well.

‍Here’s to a new year of learning, building, and striving.