Jen Bonnett From Hacker to Hustler

What came first: the hacker or the hustler? In Jen Bonnett‘s case it was the hacker. In this presentation, she tells her story of starting as a developer and CTO and how she has evolved into the role of a hustler and CEO by the hatching of a new idea – Startup Chicks. Great insights on the differences between a CTO and CEO.

Jennifer is a technology entrepreneur with over 20 years experience in Information Technology and Software Development specializing in web and mobile technologies. Jennifer has held numerous CTO positions in technology startups. Most notably, Jennifer was the co-founder and Chief Technology Officer of was an internet advertising engine similar in nature to a search engine. As the sole technology-oriented founder, she designed, developed, and launched the initial version of in the spring of 1998. She eventually grew the technology staff to 60 employees, as the company grew to 180 employees.

In 1999, was labeled the “Most Addictive” site on the web by Industry Standard; the “coolest tool site” of the year by; and was ranked number 1 in average days visited by MediaMetrix (a.k.a. the “stickiest” site on the web). By April of 2001, eTour had grown to 5 million subscribers and was ranked number 71 in total traffic for the world wide web by MediaMetrix. was acquired by Ask Jeeves (now in May of 2001.


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Thank you. When Scott asked me to talk tonight and actually try to focus me in on one role; it was difficult for me to do because I actually started out as a hacker, but now I am actually more of a hustler or storyteller. I want to kind of take you through my transition, on how started out as a hacker and how I have now become a hustler, the difference in the two roles, the difficulties that I have had making that transition, and then give you some advice about whatever role you are in.

I actually was in People Magazine in October of 2000. I am very unusual. I was a female chief technology officer. I started my career as a programmer and worked my way up to Chief Technology Officer for a fast growing dot com, one of the fastest in the country at that time. I was also a woman, which meant that I was the only woman in the room at any of these events.
I touched my first computer as a Senior in high school; when they offered the very first computer science class and I would never have taken that class had I been not forced to take it by my math teacher. I skipped math all the time. I blew it off but I got straight A’s so I couldn’t really get in trouble. And he basically said that, “I will turn you in if you don’t take my computer science class,” which was first period in the morning, second semester of my senior year. I did not want to do this but this was a TRS 80 and that’s what I learned to program on. The first computer I touched.

I am so thankful to Dr. Bretter who was my math teacher for turning me on to computers and teaching me that my job could be fun and that I could solve puzzles all day long. After college, I went to work in corporate America. I spent most of my time at Electronic Data Systems and I went through their systems and engineered development-training program after getting a Bachelors of Science in Mathematics and Computer Science. Most of these (unclear 2:25) with the exception of (unclear) were customers of EDS. So I traveled and I moved 11 times in the first three years out of college, traveling for EDS. We would basically do six-nine month projects at these large corporation and they would pick up the entire team and move us into corporate apartments for short stints to get the project off the ground.

I eventually got sick of that and left that world and joined Indis – at the time it was called TSW International. This was my first exposure to sort of a startup. It was about 100 people when I joined and it grew to about 600 people when it was acquired. The interesting thing is this is why I got into startups. I had 10,000 shares of stock that was given to me for doing programming at TSW International and when Indis bought them, a publically traded company acquired the company, all of a sudden that was worth a lot of money. And I was like “Wow, there’s something to these stock options. They are not just a piece of paper.” It was at that point in time that I was approached to cofound a startup.

My first startup was called Etor. We used to call it a surf engine. Behind the scenes it was a surf engine, a technology that I wrote and it was very much like StumbleUpon today. It was StumbleUpon before StumbleUpon existed. You would sign up for our service or just come to the site and tell us what you were looking for and we would make recommendations to you. We did so in a frameset and it was channel surfing the web, you could see one site at a time.

We grew from four cofounders to over 160 people and we raised 42 million dollars in venture capital. As Chief Technology Officer I had a staff of 60 people reporting to me and we were acquired by in 2001. So I got into entrepreneurship late but I was the hacker. We were an overnight success, people always used to tell us that we were an overnight success.
So we were founded in August of 1997 and we raised a friends and family round in January of 1998. We launched our beta in April of 1998 and we came out of beta in June of 1998. We got a new office, new name, and first real investment in the summer of 1999. We were named the stickiest website on the internet and our average time spent on site was over 20min and that was consistent from 1999 through 2001 at the time of our sale.

I just want to point out for people that don’t really know a lot about startups is that I was paid zero until July of 1999 as CTO and Cofounder. I was in a position where I planned to do this but honestly my deadline for quitting was June of 1999. My cofounders knew that there was a line in the sand that was June 1, 1999 and if we had not raised some money and we can’t get paid a little bit… my first salary was $35,000 by the way. If I can’t get that $35,000, I can’t do this anymore. Now of course, by early June we knew that the July investment was coming so obviously I never left. I rode it out and I was probably the last person standing – not entirely true. I actually went on to work for for about a year and a half.

So we raised our ten million dollar funds from what we today would call super angels. We raised all that money from people here and it was primarily individual angels that all made significant contributions to that $10 million dollars in order to keep us in town. Had they not come through we would have moved to Silicon Valley.

So when did we launch? We launched in April, came out of beta in June of 98 and October of 99 is when we had our launch party. We hit half a million subscribers in 1999 and then on to one million subscribers. So we ratcheted up our growth and then we were acquired by in June of 2001. So really crazy ride. Throughout that time we raised another 32 million dollars round before we acquired. After that I went on to work for Ask.

So what does it mean to be a hacker in a web platform in 1997? There is no cloud, no Amazon web service, no Rackspace. There are barely any colocation facilities. I collocated my first servers at MindSpring who did not have a business service. I literally called someone up at MindSpring and said I need someplace to put my servers and they said, “We have a room we can put that in.” So literally we had to buy the servers and install them. There were times when I had to call MindSpring at 4am and say, “We’re coming over! Let us in because we have problems.” So we started with one server in a wack at MindSpring and everything was done on that one server. There were no different tiers of architecture – the database, the middle tier, and the front end website was on it. That’s how we started.

I learnt very quickly that the web is about hardware, handling lots of traffic is mostly about hardware and a little bit about making sure that your database is structured right and that it is tuned. You need to make sure that your front end and code is structured properly. However, when you are talking about having three million visitors spend 20min on your site in a single hour window, then you are talking about a lot of hardware.

So this was our production network and it was in one of the presentations we had to give to as part of our due diligence. They wanted answers to what’s that special sauce and how does it all work. This was actually at the end. We had 32 load balanced web servers taking the traffic. We had about ten middle tier servers and then the primary production database servers were two big Sunsalaris machines running against an EMC data storage device. We had over a terabyte of data in 1999 so it was a huge amount of data for that time. We tracked every single site that you visited and if you came through our site and did a search, we knew every single site that you visited, we knew how long you were on it, how many clicks you went into it, and we knew whether or not you shared it with a friend, gave it a thumbs up or down. So there was intrinsic and explicit ways that we monitored whether you liked the site. You could tell us that you liked the site but we could also make an implied definition of whether you liked the site. All of that went back into delivering the next site to you so we were trying to make sure that we were delivering the absolute best sites for what you were looking for right now.

That gives you a perspective of what that looked like at the time and that’s just one of the data centers. We had a smaller data center. Then the next better one was in California but it was much smaller because it was just for a fail over situation.
I spent many nights at the data center and as Chief Technology Officer I coded on Fridays. That was my role and I always liked to stay in the code so I still wanted to code on Friday, wanted to be a hacker, know what was going on. I had skunk swerk team that worked on future projects with me. And if the team was in at 4am in the morning, then I was in at 4am in the morning with my role. So if there was something going on and somebody was going to have to make a decision whether to roll back a release or roll back a fix, it was my decision to make as CTO. So I was there.

So after doing all these technology startups, I realized that all of a sudden I have all these ideas that I wanted to pursue. The most recent ones that I have done and they started at exactly the same time (never start two startups at the same time) were StartupChicks and Nexpense. StartupChicks is a 501c3, we currently have 1350 members in 25 states. We have an accelerator program and we have had over 27 female founders graduate in the last four years. My role there is the face. I am the face of StartupChicks and most of what I do is coaching and trying to raise money. I have to sell. If StartupChicks is going to continue and live, I have to sell. I have to sell to women who are going to join StartupChicks, I have to sell to women who will start StartupChicks Chapters in other cities so we can be a global organization, and I have to sell to sponsors.

Nexpense is similar. I coded the front end of the mobile apps for Nexpense even though I was CEO. I came to the realization a year into it that I actually jeopardized the future of the business because I was doing the wrong things. If there was a bug, I was spending my time fixing it instead of making a sales call. So again, you have to be out there making sales if you are a hustler. So I made this list of hacker vs. hustler to share with you.

When I was a hacker, then most of the time it was someone else’s idea. When I have been the hustler, it’s been my idea. Hacker – I wrote the first version of the code. Hustler – I still did it the last time but no longer. Wire the office, fix the printer. One of the dirty little secrets is that if you are the Chief Technology Officer of a company, it does not matter that that is the title. If the printer is broken and the CEO is trying to print out slides to take to an investor meeting, you better fix that printer now. Drop everything to fix the printer because that meeting is really important.

As a hacker, especially when closing money with investors, I was the closer. This is important. As a CTO for a startup, the business people have already met with the investors so you are the last person on the team that the investor meets with. And if you say something different, or you are not confident that you can achieve the mission, you will not get that money. So you are the closer of that round.

As a hustler, I am the cold caller trying to make both sales and raising money. Before I grew a tech team I was really focused on the people, now I am growing the company and so money is more important for me right now. I have to make sure that I have cash flow so that my people can build their teams. I am the face of the company before I was the architect and problem solver. So no matter what they say, it’s always a 24/7, 365 job. As a hacker I had a lot of time to strategize and plan, now I have no quiet time.
As a CTO my job is to be the pessimist. My job is to figure out what’s going to cause something to break before it breaks, or have a plan to fix it so that it does not take us down. If you are making 10 – 40,000 dollars an hour at 0.20cents a click, you cannot be down. As a hustler you’ve got to be the optimist and always looking at the positive signs. “We are going to get through this.” So there are two different sides of the world. Both are lonely jobs – not going to lie to you.

You’re the CTO – you are up at 4am in the morning and trying to figure out how to solve the problem or your team is trying to figure out how to solve the problem. It’s a lonely job being a CEO because what if you are running out of money. Can I make payroll this week? How many people should I tell that I might not make payroll payments. It’s a lonely job.

Another thing. The hacker usually stays at exit. I was at for two years afterwards. But as a CEO, my company got acquired and I was gone three weeks later. So different roles and it’s something to think about. Who are you? It doesn’t really matter. Pick a role and go for it. Be the best CTO you can, be the best CEO you can. Have clearly defined roles in your founding team. It’s great through customer discovery that you need to have everyone on the same page but then divide and conquer. Fully commit – this is a 400% effort. Have a startup prenup. Have a conversation and have the tough questions answered. Know what’s going to happen if someone gets sick or hit by a car and decides to drop out in two years. What are you going to do with the company? Lastly, just enjoy the ride. It’s awesome, fun, crazy, there is a lot of adrenaline. There are highs and lows but it’s awesome. That’s all I have for you. Thanks.