Authentic &


Matt Douglas, Founder and CEO of Sincere Corporation

Five Lessons After Five Years of Punchbowl

Five years ago this week, I was part of a small team (me, Sean, Devin and Gerard) that launched (now The site officially “launched” with a press article that was published on the tech blogger site Five years. Wow.

I’ve been thinking a lot about what this anniversary means for me professionally and personally, and some of the most important lessons I’ve learned after these five years. So here are five big lessons, in no particular order:

1) It’s going to take much longer than you think

When I started Punchbowl, I had no idea how long it would take to build the company. In fact, I didn’t even know if it would become a real company. Now five years later, I realize just how long it takes to build lasting value. It takes longer than you think to build a great team, to evolve the product, to build revenue streams, and to delight your customers. You hear about a lot of companies that are overnight successes, but that’s rarely actually the case. Most start-ups slog away year after year, and then the media glorifies their rise to the top. It take most companies 5-10 years to become a financial success (e.g. Constant Contact took 11 years before it went public, hardly an overnight success). So here’s the real question: will I be running Punchbowl five years from now? I have no idea. But I’ll tell you this: if I am, we’ll have experienced more success than I could have ever predicted.

2) No one will believe in you more than yourself

For anyone reading this post and contemplating starting a company — let me give you a piece of advice. Stop seeking outside validation for your ideas and beliefs. Will you find some people to agree with you? Absolutely. And you’ll also find some people that tell you that you’re full of shit and you don’t know what you’re talking about. The reality is that the only person that needs to believe in you for the entire journey is yourself. Yes, I’ve had lots of days that I wanted to throw in the towel and get a simpler job. But deep within my soul has always been a belief in myself and a belief that the world needs the products we’re creating. And that’s critically important if you’re going to succeed as an entrepreneur.

3) Don’t beat yourself up too much when things are going badly

I don’t remember where I heard it, but I love the saying “Don’t beat yourself up too much when things are going badly, and don’t congratulate yourself too much when things are going great.” If there is one start-up maxim that I try to live by, it’s this one. I’m lucky to be surrounded by a few people in my life that are more “even-keeled” than I am (hi Sean and Jess). As a passionate startup entrepreneur, I find it hard to keep my emotions in check when things are going badly. Somedays it feels like it’s all going to come crashing down on me. And other days are filled with great success. On those days, it’s hard not to be on top of the world with excitement about the possibilities. From my experience, the key to success as an entrepreneur is to remain as balanced as possible through the ups and downs. Ask anyone who works with me: this is much easier said than done.

4) Great people are the lifeblood of your success

It’s taken five years to build, but we now have a *great* team at Punchbowl. I can’t emphasize enough how important it is to find people that are “A” players that fit well with your style. When you find them, do what it takes to keep them. I believe that one of my strengths is my ability to spot talented people and form lasting relationships. A good example of this is the friendship I formed with a guy named Eric during business school. When I met him, I knew he was very smart. Years later (wow, 10 years!) Eric is a key member of the Punchbowl team and a big part of the reason that we’ve been successful these past few years. If you want to be a successful entrepreneur, seek out the smartest people you know, form lasting relationships, and convince them to join your team. And if you make some mistakes along the way, it’s also important to quickly remove people who aren’t working out. In every single case where I laid off an employee or contractor, I wish I had done it sooner. Final thought: regardless of how much talent you possess, it’s very unlikely that you’ll build a successful startup alone. Go find great people that want to work with you and who respect you. After all, there’s no greater success than the admiration and respect from your peers.

5) The journey is the reward 

Yes, I know it’s a trite saying, but the more this journey continues, the more I realize it’s true. I started Punchbowl with the desire to have freedom in my career and in the hopes of making significant money someday. While it’s true that I still want both of those things, more and more I find myself relishing the journey. I take great pleasure in customer stories, and how we’ve made their lives better. And these days I spend more time focusing on strategy and product direction. These are the things I really enjoy and I’m pretty good at them too. I like my co-workers, and I generally like what I do (ok, minus the legal stuff). Now that the company has grown bigger I have more resources — and that makes daily challenges that much easier. I’m acutely aware that someday I will look back on these years as the glory days of my first start-up. It’s been challenging and fun, and I wouldn’t trade it for any other job in the world.

Happy 5th Birthday Punchbowl. Thank you for everything you have given me over these last five years. Thank you to the people who helped create Punchbowl, and the customers that pushed us to make the site better everyday. What an amazing ride it’s been.

©2023 Matt Douglas