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5 lessons learned in 5 years of building OpenPhone

OpenPhone fifth birthday

OpenPhone turns 5 years old today. 🥳

It feels like these five years flew by, but I know we’ve been through a lot. I sometimes wonder — what would I have done differently if I could go back? What do I wish I knew before embarking on this journey?

So as we celebrate this milestone and in the spirit of paying it forward, I’d like to reflect on our journey and share five things I wish someone told me when we started OpenPhone. If you’re a fellow founder, I hope this helps you or offers another perspective on the journey from incorporation to Series B.

1. Bet on motivation over experience.

Hiring is everything because people are everything. And hiring is incredibly hard.

I don’t have any cheat codes for hiring, but if I could tell myself one thing, it would be to bet on motivation over experience.

Startups are filled with all types of challenges, and no amount of experience will help someone overcome these challenges if they lack internal motivation.

This motivation can come from a passion for the company’s mission or the product. It can also come from an internal desire to prove to themselves that they can succeed.

What I’m saying is that every startup needs people with a chip on their shoulders to defy the odds and shape the trajectory of the company. So while hiring is highly contextual and depends on circumstances, I would always bet on someone with a stronger internal drive vs deeper experience.

2. Don’t bite off more than you can chew.

What’s one competitive advantage of any startup? Speed.

Startups can go from an idea to releasing a feature to production in an afternoon. Unlike the incumbents, startups can make rapid decisions and even change direction overnight.

This rapid speed is harder to maintain as the company grows. It also gets more challenging if you introduce complexity before you can properly absorb it.

For example, at some point after we raised our Series A, a web agency we hired convinced us to move our website hosting from Contentful to Webflow. The idea was that we would be better served with a more advanced and flexible CMS solution.

What we didn’t know about this decision was that we’d need a lot of Engineering resources to make changes to our website. At one point, we got blocked for weeks due to a backlog of landing pages that we needed to ship!

This isn’t, by any means, a Webflow versus Contentful example but rather an example where our small startup tried to “grow up” too fast and move to a solution (and a process) we just couldn’t handle yet.

The lesson here is: Whether it’s picking a robust new tool you’re not ready for yet, adding too many steps to your new hire onboarding, or even choosing to build a feature you can’t continuously iterate on, choose the path that doesn’t compromise your #1 advantage — speed.

3. Get on a texting basis with customers, investors, partners, and candidates.

When it comes to relationships, texting > email.

Admittedly, I may be a little biased. 🙂

But hear me out on this.

Most founders I know have their key customers, investors, partners, and candidates a text message away.

One notable example is Deel’s CEO and Co-Founder, Alex Bouaziz using a 50-person WhatsApp group for product research. As a Deel customer, I can confirm that Alex is incredibly fast to message back.

Whether it’s getting brutally honest feedback on a feature you’ve shipped, a request for an intro, or moving a deal across, it’s a lot harder to do without a relationship to fall back on.

And to me, an easy proxy for whether there’s an established relationship is whether or not you can text someone (and, of course, they text you back!)

4. Carve out time in your day for things you get energy from.

No day is the same when you’re building a company, but that also means, at some point, you’ll find yourself doing work that doesn’t always bring joy. Tax filings, anyone? 😅

I stay energized by intentionally making time and space for work that feels like play and gets me excited. For example, I find contributing to our blog very joyful. In particular, when it comes to sharing lessons learned and offering a window into the OpenPhone journey, like in this post on getting our first 1,000 customers or this one about hiring lessons learned.

Writing this very post has been a ton of fun for me, too.

I am able to help our marketing team with content creation and, at the same time, recharge my creative batteries. Win-win, or as we say at OpenPhone — feeding two birds with one scone.

5. Take care of yourself.

Startup founders are often celebrated for their hustle and relentless pursuit of success. I resonate with these qualities very much. In fact, being relentless is one of OpenPhone’s company values.

At the same time, continuously sprinting without taking breaks is mentally and physically exhausting.

I find that taking time to properly recharge allows me to come back with renewed energy and perspective. I can see the problem from another angle, come up with an unusual idea, or get myself unstuck.

While it sounds like this is something I’m doing for myself, selfishly, I find it makes a meaningful impact on my team, customers, and anyone I work with. When I’m rested, I’m a better listener and communicator and able to build better relationships.

Looking back on my reflections from OpenPhone’s time at Y Combinator, I’m realizing that I had this realization fairly early. It’s one lesson I keep reminding myself about. 😊

“Most people overestimate what they can do in one year and underestimate what they can do in ten years.” – Bill Gates

I hope this perspective is useful to you as go through your entrepreneurial journey. If I can help in some way, don’t hesitate to reach out.

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