A Decade in Review: 3 key takeaways from my 10 Years at Ditto

I cofounded Ditto ten years ago this month. It’s kind of crazy when I take a step back and let that sink in. It’s not lost on me that most startups don’t last that long and I’m insanely proud that we are still standing despite, quite frankly, an absurd amount of obstacles. These obstacles have been part of why Ditto has been such an extraordinary learning experience for me.

As I reflect back on the past decade, there are a few big takeaways that I hope help other entrepreneurs, leaders and investors can learn from:

  1. Focus on the people
  2. Values come first
  3. Be a cockroach

Focus on the people

Make no mistake, entrepreneurship is a team sport. More than the achievements and hurdles, my reflections on the past decade go straight to the long roster of people who have built Ditto with me – many of whom worked their tails off for several years before moving on, some of whom I had to let go during hard times or strategic shifts, and some who are still by my side. I’m so grateful to each of them. I have also learned a lot about what worked and what didn’t.

To get the people-side of your business right, I recommend being incredibly intentional with your culture so you can identify the type of people who will thrive in your organization and which people won’t. I think that all starts with a tight, specific vision of the kind of team and culture you want to build.

In my early career, I spent time on Wall Street and in private equity and suffice it to say that the culture wasn’t a place I wanted to stay in. I moved out to the West Coast to attend business school but quickly realized that some of what I didn’t like about finance seemed to also be true with many venture-backed Silicon-Valley tech companies: bro/masculine cultures and aggressive, arrogant male founders/leaders worshipped as heros who just didn’t seem like the kind of people I wanted to work for. I fell in love with the idea of a female-founded and led organization with a really healthy culture and a team full of competent, kind, diverse people. I have a very clear vision of what this looks like and ensuring this is our reality remains my primary motivation 10 years later.

Values come first

I have made so many mistakes — big and small — since starting Ditto (cue #cringechallenge) but I am proud that we are doing a lot right on the culture side. Pre-pandemic when our office was still open, it was the kind of place where we all ate lunch together not because it was paid for by the company or mandated but because we hired passionate, friendly people who were fun to eat lunch with. I also think on the whole we’ve hired people who are adaptive which has really helped as we’ve shifted the culture virtually and more globally distributed this past year.

We’ve dialed-in the kind of people who are a great fit for our culture and are no longer afraid to let go of people if they aren’t a good values-match, even if they are really competent. Admittedly the last part is hard and took much longer to have the confidence to do this. Culture, values and people are intertwined and it’s important to be purposeful and thoughtful about all three.

You might be surprised that I haven’t actually mentioned eyewear yet. It seems to me that a lot of entrepreneurs focus primarily on their company’s mission statement. I believe that values are greater or equal in importance to the mission. Our values shown aren’t just words on a paper. They describe the kind of people we recruit and retain. They describe how we make decisions and prioritize projects. They describe our culture.

We are inventors.

We celebrate what makes us different.

We are in this together.

We are built on trust.

We are passionate.

Now don’t get me wrong, Ditto’s mission to make buying eyewear more personalized and accessible resonates deeply. I think it’s a worthy goal to help a very traditional category execute a digital transformation that will have broad sweeping benefits for end customers that increases accessibility and affordability and celebrates personalization and what makes each customer unique. But it’s the combination of the what (our mission) and how (our values) that keeps getting me out of bed every morning excited — even after 10 years.

Be a cockroach

I can only tell the full, dramatic story of Ditto accompanied by a hangover-inducing amount of booze. The short version is that right out of the gate, we were hit with two nasty lawsuits over IP that took us 4.5 years to resolve. This caused scrappy pivots and even scrappier fundraising. We had to lay off incredibly talented team members. We took investments from clients in exchange for exclusivity rights which then hurt our sales for years to come. I went years without a salary and asked my team to work for way-below-market wages. In a bizarre turn of events, we even did a deal with a notorious patent troll to defend us against the other suits. My lawyers smirk every time we bring them business deals with “creative” structures. I even have one investor who calls me a cockroach because I just won’t die.

I’m incredibly proud of our resiliency. Our passion, adaptiveness, and grit are the reasons we still exist. The Ditto story is a reminder that when you keep working hard and build meaningful relationships with clients, new options emerge.

This flies in the face of the popular “fail fast” mantra. I liked the idea of that but in practice, every “we’ll know in six months” for us was left in the gray area. Decisions had to be made in the absence of data-driven clarity and in those moments, we chose to keep fighting. I will admit that if I only cared about financial outcome maybe there was a different, more optimal path. But I can tell you optimizing merely for the financials isn’t the way to rally the troops behind you. Passion and vision is what people want to follow. It’s that culture, shared by every single member of our team, that makes Ditto something special.

And while the full extent of Ditto’s success remains to be seen, we’ve far exceeded most people’s expectations and the future is looking brighter than ever. So my advice is to find a way. Pivot. Structure a creative deal with cash upfront. Talk to clients about investing. But, never give up… be a cockroach.

Conclusion

The last decade running Ditto has been an extraordinary learning opportunity for me. I don’t regret the mistakes and missteps (too much) because they’ve taught me a lot. I have so much more clarity on the leader I want to become and the culture we want to foster. As Ditto continues to scale and moves increasingly distributed and global, I’m excited about my next big challenge: keeping our people prioritized, our values strong and disseminated, and our passion and resolve stronger than ever even as we scale.

If you’d like to follow along on this journey you can follow Ditto and connect with me on LinkedIn. You can also read the full 10-year anniversary press release here.

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