Lessons I learned as a first time CEO

I never intended to be a CEO; my first career was in television production. But when I stumbled upon something I loved — really loved — and realized it could be a successful business, I started my own company and never looked back. I founded Three Day Rule, a tech-enabled white glove matchmaking service, initially because setting up my friends was a personal passion, but eventually because I saw a huge hole in the dating market. Two rounds of fundraising, a partnership with Match.com, 30 employees, and countless happy couples in seven cities around the country, I’ve learned more than I could have imagined about running a company. Becoming a CEO happened by chance, but after three years of running a start-up, I now know what it takes to be a strong leader for a growing company.

Here are a few tips and techniques I use to run my business:

CEO 1:1's

Every quarter, I do 1:1’s with every single employee on my team. With an increasing number of employees, this takes up more and more time, but I still make it a priority. Many CEOs delegate 1:1s and performance reviews to mid-level managers, but there is no better way to improve your business than to hear feedback directly from your rank and file employees. You’ll be surprised at how honest they will be with you, and how muddled information can become as it moves up the chain. Most importantly, your team feels that their input is valuable, which is directly correlated with their happiness at the company.

I’ve gotten better at conducting 1:1s over time. I ask different questions every quarter and no one gets questions ahead of time. My goals are to get a real read on their satisfaction, discover opportunities for growth, and gut check my own decision-making processes. Some examples of questions that I ask:

- How long do you envision staying at TDR?

- What position are you working towards?

- What holes do you see in our company today?

- What is one piece of technology that would help make your job faster?

- Tell me about your relationship with your manager. What are his/her strengths? What can he/she improve?


One of my biggest wins has been partnering with companies that are much bigger than mine. It sounds obvious, but oftentimes startups will ignore partnerships, focusing on building their core business and user base without recognizing there could be easier wins. When I first reached out to Match/IAC, I knew they were the power player in the dating space, and people told me Three Day Rule was too small for them. But I knew that partnering with organizations that had paved the way was an opportunity to get more resources and scale faster, so I kept after it and my determination paid off.

Another benefit of pursuing strategic partnerships is that it forces you to define your product or service in relation to other players in the market, and may encourage you to develop a synergistic offering that adds value to both the dominant market players and end users.


Equity is a big deal so make it a big deal. Not everyone, especially young employees, understand this. When you present an offer, tell the team member how valuable they are and that is why they are getting equity. Set expectations, and explain what having equity implies, so they feel ownership over the company’s goals. Equity can be a powerful motivator, but only when the employee understands how and why their part is valuable.


Opinions are data points. When I first started as a CEO, I took in every opinion, listening to each detail and letting them affect me. I now know that opinions can often be the opposite of facts, but that each becomes a valuable data point upon which I can make decisions. Listen to feedback, especially from advisors and people you respect, but make decisions for yourself. Everyone thinks they can solve your challenges but you are the only one who really understands all angles. Don’t be afraid to go with your gut — even when it means rejecting an important stakeholder’s opinion.


It’s easy to get caught up in the big goals. Most companies celebrate when they close funding, hit profitability, reach their millionth users or become acquired. These milestones are obvious, but it is also important to acknowledge and celebrate the small wins in between. Every Monday, we have a team meeting with every employee across our seven cities. I start with “shout outs” for the week and praise members of our business team for big weekly accomplishments and then the matchmakers for their successes. For our company, this can be a couple who decides to date exclusively or a couple who goes on their 3rd date. These may seem insignificant in the scheme of running a company, but it reminds the team that all of their work is equally important and that we are all passionate about helping our clients find romantic connections.


Give your employees opportunities that should really be for you. As a CEO, you’ll be given many opportunities to speak on panels, give press interviews or even be on television. It is a leap of faith to put panels and press in the hands of your employees, but they learn quickly, feel valued, and get excited about the exposure. You’ll learn about strengths and weaknesses you wouldn’t otherwise see — perhaps someone is amazing on camera and you can use them for video content. Moving away from the spotlight can be a test of one’s own ego, but I have found that some of my employees thrive in these situations and end up being much better than I would in certain situations.


Allow employees to get to know you. They will feel more connected to you and stand beside you more than if you were just their boss. Recently, five co-workers signed up for a 6-week personal training boot camp. I suffered through planks and push-ups with junior matchmakers, and it was a bonding experience. My employees feel like they know me and trust me, and sharing each other’s personal pitfalls and celebrations can tie a team together.

Over time, I’ve learned more than I’ve ever thought possible about being a CEO. I still have a lot to learn, but hopefully my lessons can help those who are just starting out. Take smart risks, be aware of your actions, and think about others first. And don’t forget to look back and reflect on what you’ve learned along the way.