Hello and welcome to another edition of Founder to Founder 👋

OpenPhone turns 7 years old today.

That’s like having a second grader. Crazy!

I’m going through highs and lows in my head as I type this and it’s one heck of a rollercoaster. Reflecting on those, I am filled with gratitude for our team and customers for being there through them.

Two years ago, when OpenPhone turned 5, I wrote about five things I wish someone had told me when we started.  Now, with two more years of experience under my belt, I was curious to look at those lessons with fresh eyes.

Today, I want to revisit those lessons and see if they still hold up. Some do, but others...well, I've definitely gained some new perspectives. As founders, we're constantly learning and evolving. Looking back at my own advice from just two years ago has been a fascinating exercise in seeing how my thinking has changed.

I hope these reflections offer you some value on your own founder journey.

Let's dive in!

📒 DEEP DIVE

How 7 years of building a company changes your perspective

Honest reflections on 7 years of OpenPhone, and how my thinking has evolved

Some of these principles have stood the test of time, while others deserve a more nuanced perspective.

Let's break down what's changed and what hasn't as I've grown alongside OpenPhone:

1. From "Bet on motivation over experience" to "Find people who have both"

Two years ago, I wrote that if I had to choose, I'd "always bet on someone with a stronger internal drive vs deeper experience."

I still believe motivation is important. A startup is filled with challenges, and no amount of experience helps someone overcome them without strong internal motivation.

But here's where my thinking has evolved: This creates a false choice.

As OpenPhone has grown, I've met many people who have both incredible motivation and valuable experience that helps us see around the corner.

When I wrote that original advice, I thought that it should be a choice.

Now I know better: don't settle for one or the other. Look for motivated people who have also seen what great looks like in their domain.

Someone who has both drive and has witnessed excellence firsthand brings something special. They're not just energetic and committed, they also have a vision for what success in their role actually means.

2. "Don't bite off more than you can chew" — With team alignment, you can actually do more

In my 5-year post, I emphasized that speed is a startup's competitive advantage, and taking on too much complexity can slow you down.

I still believe that's true, but with more nuance now. The real question isn't about ambition, it's about alignment and foundation.

When I wrote this, I didn't consider that with the right clarity, alignment, and processes, you actually can be more ambitious.

If your team has good alignment, clear goals, and established processes, you can tackle bigger challenges without things falling through the cracks.

Looking back at OpenPhone's journey, we've had periods where our tiny team shipped an incredible amount, followed by periods where our larger team shipped much less. Now we're at a place where our larger team is shipping more than ever before.

When we weren't shipping as quickly, we needed better goal-setting and coordination, not necessarily more people.

With Sona, our new AI product, we were very ambitious—but we were also very clear about what we were building and why. When you have that foundation, you can aim higher without everything collapsing.

So what I'm really saying is be as ambitious as you want, but make sure your team is aligned on goals and good coordination. With that foundation, you can take on much bigger challenges without everything falling apart.

3. "Get on a texting basis with customers, investors, partners, and candidates" — Took this even further

In my 5-year post, I made the case that texting beats email when it comes to relationships. I talked about how I always text with customers, investors, and partners. I've doubled down on this advice completely. In fact, I've taken this principle much further in the last two years.

I'm on Reddit probably too much, actively monitoring mentions of OpenPhone. I've volunteered my email for all the "no-reply@" email responses. I've made myself accessible to customers, investors, and team members through multiple channels.

This direct connection with people using and interested in our product has been invaluable. It keeps me grounded in real feedback and genuine interactions.

So yes, this lesson still stands strong—and I've leaned into it even more than when I first wrote it.

4. "Carve out time in your day for things you get energy from" — Lean into your unique strengths

In my original post, I talked about making time for things I find joyful, like writing blog posts, to "recharge my creative batteries."

While I still think this is true, my perspective has changed. It's not just about doing things that give you energy, it's about identifying what you, as a founder, are uniquely skilled at and making sure you don't lose that as your company scales.

I didn't start creating content just because it was fun (though it is!). I did it because I realized I could uniquely lend my founder perspective to extend our brand's reach.

This has real business impact.

As companies grow, founders often step away from their areas of strength. A product-focused founder might give up product involvement too quickly. A sales-focused founder might step back from customer conversations too soon.

I've found content creation enjoyable, but more importantly, it's something I can do that has a specific and valuable impact on our business that others can't replicate in quite the same way.

For example, I’ve had great feedback on this newsletter from our customers (thanks for reading!) and writing it helps add more value to them while getting us in front of new audiences.

5. "Take care of yourself" — A very different reality as a new parent

When I wrote about proper rest and recharging two years ago, I wasn't a mom yet. But now that I am, “Take care of yourself" has a different meaning.

The idea of "recharging" I had then feels almost like a luxury now.

With a little one, my time is now divided between work and family. There's not much room for anything else.

Becoming a parent has been a true forcing function. I no longer have the luxury of working 24/7 or casually dipping in and out of work mode.

When I'm working, I'm fully focused because I have to be. When I'm with my family, I try to be fully present there too.

Before, I technically could work without constraints. Now, having constraints has made me better at focusing on what truly matters instead of trying to do everything.

Two bonus lessons I've learned along the way

6. Sometimes you can't choose between competing priorities — you have to do both

During our Y Combinator batch, I remember Mahyar and I asked our group partner, Michael Seibel, for feedback when we were debating whether we should build features to help acquire new customers or retain existing ones.

His answer was essentially: tough luck, you have to do both.

While there's a lot of advice out there about focusing on one metric or priority, I've found that some things are more interconnected than they first appear.

Looking back at OpenPhone's most pivotal moments, many of them transformed multiple parts of our business.

For example, when we launched OpenPhone for Teams, it helped us acquire new team customers while also retaining existing customers who were growing into teams.

The same goes for integrations—they bring in new customers who use those services while also helping us retain existing customers who want those connections. A recent example of this—our integration with Jobber.

So while it’s nice to be able to focus on one thing, the reality of founder life is that sometimes you can't choose, and it’s OK.

7. Understand "what great looks like" as early as possible

I don’t remember who introduced me to this concept, but understanding "what great looks like" in every area of the business is hugely underrated.

Sometimes the highest leverage thing I can do as a founder is help us understand what great looks like, or as our Director of Sales, Melissa Bates, put it the other day (WGLL)

This might mean talking to experts in that domain, bringing on advisors with relevant experience, or hiring team members who've experienced a certain scale firsthand.

For example, I have a Gmail folder labeled "email inspiration" where I save any great emails I receive, whether cold or lifecycle. Allows me to keep educating myself on where the bar is at.

So in every aspect of your business, from product design to team communication—ask yourself: "What does great look like here?" The answer will guide you much faster than figuring it out through trial and error alone.

What’s next

Looking back at my lessons from 2023 is a humbling reminder of how much we're all constantly learning as founders.

Some of what I wrote back then still holds up, but with deeper nuance. Other perspectives have shifted dramatically as both I and OpenPhone have grown.

I suspect in another two years I'll look back at this post and cringe a little 😅.

That's part of the journey.

One unexpected benefit of creating content is that it gives me these time stamps to look back on. It helps me track my own growth in a tangible way that would otherwise be lost to memory.

Until next time, and happy birthday, OpenPhone!