As many have mentioned, the CEO role varies a ton from company to company, especially based on size.
I think it is pretty well known that CEOs wear many hats. But the challenging part is as CEO, you have to figure out which hats - out of thousands and thousands of options - to try on! There are always a million things you can be doing as a CEO, and so a lot of my time has been spent ... trying to figure out what is worth spending my time on. Every month or two, I take on a new role, and then I try to figure out if that role is vital to our company, and how to structure the role, so that I can hand it off to another member of the company and look for a new hat to try on.
It's definitely hard to explain what a CEO does in a nutshell. I figured the easiest way to explain what it's like being CEO is just to give a timeline of the different roles I've taken on, since starting Dating Ring as a sole founder in April 2013.
April - May 2013: Evangelizing, emails, and spreadsheets
At this point, I was emailing everyone I knew to see if they wanted to be users of my [then nonexistent] dating product, and asking them to refer all of their friends. I was going out 4-5 nights a week and meeting new 'users' at bars in NYC. I was doing a lot of market research to find out what people liked and didn't like about current dating products, and what they were looking for in a new one. I was collecting a lot of email addresses, and emailing everyone once or twice a week to tell them about what I was learning, and keep them excited ... while no product existed.
June - July 2013: Strategizing, forming the corporation, and cofounder dating
I was doing small scale tests of Dating Ring's MVP (minimum viable product) by sending out a few group dates a week and then speaking to users about how they went. I was in talks with a few people interested in being my cofounders. I spent a lot of time speaking to each potential cofounder about their background and what they would bring to the team, and figuring out how to split equity. I also found a lawyer and accountant and registered as a C Corp in Delaware.
August - September 2013: Accelerator research and creating our pitch
I spent hours and hours for a number of weeks tweaking and refining Dating Ring's 'elevator pitch'. I was pitching at a lot of different startup pitch events, as well as working on applications to a number of startup accelerators.
October - November 2013: Product development and interview preparation
I worked a lot with our first engineer on creating a basic technical prototype of our group dating product (hosted on Zoho, rather than built ourselves) so that we would have the ability to schedule dozens of group dates each week, rather than a handful. I also spent an entire month researching Y Combinator and preparing for our interview.
December 2013 - March 2014: Y Combinating and Growth Hacking
After Dating Ring got into Y Combinator, I immediately moved out to Mountain View, and essentially started YC a month early. I had four months to achieve as much growth as possible before fundraising. A lot of my time at YC was spent 'growth hacking' - trying out a new marketing strategy every week, measuring the results, and then either refining the strategy and automating it (if it worked) or ditching it and starting again (if it didn't). This involved everything from preparing our launch in San Francisco, to spending 48 hour creating a video announcing a crazy plan to do cross-country matchmaking, to doing a ton of PR around that trip.
I spent a good amount of time during these months doing what I had done in my very first few months of Dating Ring - evangelizing and meeting new members in SF. I also spent a ton of time brainstorming with my cofounders and trying to figure out what our product should be. We tested out a few small product pivots before switching from group dates to 1-on-1 dates.
April - May 2014: Fundraising
Fundraising is easily the least fun part of being CEO. Basically, I was going through LinkedIn and AngelList, finding investors who might be interested in the dating space, and contacting friends for warm intros. Then I was going to meetings, going through our pitch deck, and sending lots of follow-up emails. I was also revising our pitch deck pretty much every day.
June 2014: Sleeping and watching TV
At this point, I was pretty burnt out. My official job as CEO was to take a break, refresh, and become a super passionate CEO again. So I watched all of House of Cards and Orange is the New Black and slept a lot.
July 2014: Restructuring
Our team had grown from 3 to 7 and we were on two coasts. Things had gotten pretty messy, so I spent most of this month speaking to partners from Y Combinator about how to best move forward. I did a lot of re-organizing that month. I did some hiring and firing (also no fun), set up bi-weekly meetings, standardized company agendas, and created a solid game plan for the next 6 months. I also created financial projections and a budget for the rest of the year. And I created a new part of the company - a more personalized, VIP matchmaking service - as an additional stream of revenue.
August - September 2014: Product Design and Launch Preparations
These were easily my favorite two months of the company - or maybe my entire life. After bringing on a new engineer, we started our product from scratch. We threw away all of our original ideas and went back to the drawing board. After doing an extensive survey of our users, I spent a few weeks with my cofounder sketching out every feature we would want and figuring out the user flow. I then worked pretty much 24/7 with our engineer. I also became a designer for the month, which was fun, as I had never designed anything before. At the same time, I was planning our launch - the email I was going to send to our users, and a PR strategy to bring new users in. I acted as a journalist, ran interviews, and created my first Press Release.
October 2014: Launch
Actually, this was probably my favorite month of the company. I spent the early part of the launching doing PR and speaking to reporters. Any time we build a new feature, I spend at least a week or two doing every part of the process. On our new app, this meant I was playing matchmaker and setting up matches. Every day, I was analyzing our revenue and conversion rates, and trying to figure out how to optimize conversions. During one all-nighter, I made a huge change to our business model (based on customer feedback and suggestions from my cofounder), and we changed from a product where you had to pay to play to a freemium model.
November 2014: Product Improvements
I spent a lot of November creating matches, and coming up with ways that our engineer could improve the admin side of our product. I also dabbled a bit in data analysis and algorithm enhancements. This was probably the time when I felt the smartest.
December 2014: Writing and Growth Hacking
It's mid-December now, so I'm still figuring out exactly what I will be focusing on this month. The first half of the month I spent writing blog posts and reading everything I could get my hands on regarding growth hacking. I launched a giveaway to try to gain new subscribers, and I've spent a lot of time in meetings with the company, figuring out how to make the first major changes to our product based on user feedback.
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