BTU #157 - Employee #500 at Aol (Rob Shenk)

"One of the great things about AOL was the networking. I really got to know the Who’s Who list of personal finance and investing. You could kind of see who the winners were and who was shaking out towards the top. E*Trade, who I met when they were tiny and operating out of a small office, eventually became this behemoth. They had grown into this really formidable firm.”
- Rob Shenk

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Rob Shenk is the Senior Vice President for Visitor Engagement at George Washington’s Mount Vernon. Originally from the San Francisco Bay Area, Rob graduated from the University of California at Berkeley. After graduating from Aviation Officers Candidate School and Intel school, Rob joined Strike Fighter Squadron 147 (The Argonauts) as their strike intelligence officer, where he deployed to the Far East and Persian Gulf onboard USS Nimitz. Days after leaving the Navy, Rob joined a then-relatively small company called America Online where he rose through the ranks to become the Vice President of AOL’s Personal Finance Channel. After leaving AOL, Rob joined E*TRADE Financial where he eventually rose to manage all the online banking services and cash management products. Rob left E*TRADE to join the Civil War Trust as their first Director of Internet Strategy and Development. He holds a Master of Arts in National Security Studies from Georgetown University and currently lives in Alexandria, Virginia. His son is currently a midshipman at the United States Naval Academy.

Why to Listen: 

This is a terrific episode for any member of the Armed Forces. Rob joined Aol as their 500th employee and was there for their growth to over 10,000 employees. He went through a similar process with eTrade. But he got his foot in the door, directly out of the military, by applying to be a customer phone support person! His story is one of failing and taking risks, or being part of an internet revolution, and continuing to change his career path over time. I found his story inspiring and hope that you do as well.

Our Sponsor: 

  • StoryBox - People trust each other more than advertising. StoryBox provides the tools and supports businesses need to take the best things customers say about them, and use them to drive more sales and referrals. StoryBox offers a 10% discount to companies employing veterans of the US Armed Forces.
  • Audible is offering one FREE audio book to Beyond the Uniform listeners. You can claim this offer here, and see a list of books recommended by my guests at

Selected Resources: 

Transcript & Time Stamps: 



Joining me today from Alexandria, Virginia is Rob Shenk. I want to thank one of my advisors from StoryBox, Bill Youstra, who recommended Rob and knew Rob from their time together at AOL. I want to give a brief background on Rob which is quite impressive. He is currently the Senior Vice President for Engagement at George Washington’s Mount Vernon. Rob grew up in the Bay Area and went to school at UC Berkeley. After graduating from Aviation Officers School, he joined Strike Squadron 147 as their strike intelligence officer. Days after leaving the Navy, he joined a relatively unknown company at the time – America On Line. He rose through the ranks to eventually becoming Vice President of AOL’s personal finance channel.  After leaving AOL, Rob moved to E*TRADE where he rose to manage all online banking service. He then left E*Trade to join the Civil War Trust as their Director of Online Development. He holds a Master’s degree in National Securities Studies from Georgetown University and currently lives in Alexandria, VA. His son is a 2nd Class Midshipman at the Naval Academy.


How large was AOL when you first joined them?

It was in February of 1994 and it was pretty small – about 500 total employees. And most of those were call center service folks. So maybe about 100 in business development, software, and marketing.


When you were leaving the Navy, how did you hear about the position at AOL?

I had long had an interest in personal computers throughout the 80s and 90s. Being an intelligence officer, information gathering was in my blood. In AOL’s case, I realized that they were in my backyard. I did my last tour in the Washington, DC area and I started thinking about what I was going to do afterwards. I decided I didn’t want to go into government work so I started to look beyond that. I was interested in AOL but wasn’t really sure what kinds of jobs they had. I saw that they were advertising for call center positions so I decided to apply for that.


You must have been the most overly qualified call center application they ever got!

I went into the interview and the interviewer paused and held up his hand about ten minutes into the interview. He wanted to send my resume along to other parts of the company with open positions. So it was really fortuitous that my resume ultimately ended up on the desk of Katherine Borsnick and she brought me in and hired me to work on AOL’s new personal finance channel.


One of the things I really admire about your story is that I know from doing so many of these interviews is that it can often be difficult for people to leave active duty and take a step back in terms of pay and responsibility. I admire that you were willing to roll up your sleeves and do whatever it took to get your foot in the door.

I remember I took that job and it was far less that what I was making as a Navy Lieutenant. AOL gave me stock options but I had no idea how that worked or what they were for. So I was just a young person that was willing to take a risk. One of the things I would applaud myself for doing is not taking the easy road. I remember arriving at AOL, I thought I would be there for a couple years and move on to business school. But then AOL grew very quickly into this behemoth. It was really interesting to see that development.


Do you have any advice for transitioning veterans that might be hesitant to take that risk?

I really recommend especially to younger folks to definitely take those risks. They’re much more difficult to take later in life when you have more obligations. So my advice is to really swing for the fences. To me, AOL was the risk I took. It ended up really paying off but even if it hadn’t it wouldn’t have been a problem. I would have just moved on to something else.


In that first year at AOL, what do you remember as being strengths from the military that you were able to apply to your job?

One of the attractive things about AOL was that there weren’t a lot of people around that had a lot of experience. So I felt that as long as I applied myself and showed up willing to learn, I would succeed. It was a very entrepreneurial, can-do environment. I learned AOL’s proprietary programming language called Rain Man. I was then able to interface with all different kinds of financial service firms. I was able to work with them to create their own user based interface. I got to work with Jim Cramer at the Motley Fool and also worked with financial firms like E*TRADE.

What was it like being at AOL at a time when the internet was beginning to take off?

It was really exciting. AOL was at the center of connecting people to online services – stock quotes, online banking, etc. It was fascinating to be there at this time. We got to work with a lot of sharp, smart people. That was important too – to try out different things and see what worked and what didn’t. It was a giant laboratory for new ideas.

Part of what gave me the opportunity to be successful was that I was not working with a ton of people with more experience than I had. So I felt that if I kept showing up and applying myself, I would be a valuable member of the team.


Do you have any thoughts or advice for someone that might want to get their foot in the door with a technology company?

I’ve encountered many veterans that have entered the various companies I’ve worked for. One of the challenges is that the military trains you to speak in a particular way. A lot of veterans use a lot of acronyms that are mystifying for people on the outside. So I think veterans can really help themselves by learning to speak in a way that will make sense to people on the outside. So look at your resume and practice describing everything you did without using acronyms.

I’d also recommend reading up on whatever industry you want to go into. There’s so much information available now that will connect you to whatever job function or industry you’re interested in. That will be impressive during the interview process when you can speak to recent things happening in the industry.

I’ve had many great experiences both in the military and on the outside. But people are always more interested in hearing about my time in the military than my time on the outside. So there will be a time to talk about your experience in the military. Just learn to tell it in a way that will make sense to civilian employers.


It seems like you started out in AOL working in finance. Did you stay with that during your entire time at AOL or did that shift?

I spent the bulk of my time there but also went into other areas such as travel and computing. But I kept coming back to finance and with good reason. It became very clear early on that personal finance and investing would be a huge winner in the internet space. It was dealing in money and real time data. All of these things partnered with the internet stock boom made it a really hot area to be in.


Can you describe how you moved on from AOL to E*TRADE?

Back in 1994 when I joined AOL, it was about 500 people. Fast forward to 2000 and it was about 10,000 people. So it had grown enormously. What had been a simple, entrepreneurial type company at the beginning had become much more bureaucratic. But perhaps what was even more worrisome was that the company seemed overly confident. If you’ve ever read the book The Innovator’s Dilemma, AOL would be a great case study for this. The company thought it knew better than others. The problem was that HTML had arrived and it was open source and not owned by one company. So it became evident that this open source style was going to dominate over our proprietary model. My frustration over AOL’s decision not to get more into HTML was the primary reason why I decided to leave. It was my good luck that I left just as some terrible things started happening to AOL’s stock price.


It seems like you had great timing!

It was good timing on my part but I didn’t have the insight you think I had! I went right from the frying pan into the fire. I joined E*TRADE in August of 2001. That was one month before 9/11 which brought on further reduction of the internet space and in terms of E*TRADE, the stock space completely changed. So I went from one set of challenges right to another set.


How did that transition to E*TRADE happen?

One of the great things about AOL was the networking. I really got to know the Who’s Who list of personal finance and investing. You could kind of see who the winners were and who was shaking out towards the top. E*TRADE, who I met when they were tiny and operating out of a small office, eventually became this behemoth. They had grown into this really formidable firm. I was very impressed so when I was thinking about where I wanted to go next, E*TRADE was one of the first firms I reached out to.

E*TRADE was quite large when I joined, they had grown pretty quickly. I can’t remember the number of employees but this was one of the leading internet trading firms.


After leaving AOL, did you ever want to go to a smaller company or did you immediately want to move to a large company like E*TRADE?

There was another job I had in between AOL and E*TRADE that was very brief. If we want to talk about failures, this would be my leading one. I went to work for a firm called Good in Silicon Valley. Good was initially in the mobile space. They wanted to create a corporate messaging platform which was an interesting space to be in because I was able to learn that it was not be the right fit for me. So I left there and went to E*TRADE. Even though E*TRADE was a large firm, it didn’t feel that way. It still felt very entrepreneurial which was exciting to me.


I appreciate you being willing to share that because failure is something veterans are often very adverse to but it’s something that oftentimes offers a tremendous opportunity for growth.

Failure right now is very in vogue in the entrepreneur space. You always hear, “Oh you have to fail”. I get that and I understand. But there’s a certain personal toll with failure too in which you become very invested in a project and it’s very difficult to see it not work. But particularly when you’re younger, taking risks and trying things out can have huge benefits down the road. When you get older, you’ll probably wish you had taken those risks when you were younger.


What was your day-to-day like at AOL and E*TRADE?

At both companies, it was a pretty aggressive working environment. You were always super busy. At that time, I had a wife and two young kids. This became a growing issue for me. When I was at E*TRADE, I would regularly come home late and eat dinner after my family had eaten dinner. That was a challenge. It was an all encompassing sort of experience. It was great but after 13 or 14 years of that, I decided I wanted to make a switch.

What I’ve learned over time is that in order to remain innovative and creative, it’s necessary not to become burnt out. I believe that being an endurance runner rather than a sprinter can be just as valuable to a company.


What kind of people were you working with at E*TRADE?

When I was first hired at E*TRADE, they were starting to acquire banking, insurance, and loans services. They wanted to group these together in a way that would allow ease of use for customers. They wanted to do this through web design. So my first job was to kind of make that happen. I worked closely with our software and design teams to create this. was then asked if I wanted to take over E*TRADE’s financial services. It was an interesting challenge but it was really fun. At that time online banking was going through a huge growth and renaissance.


After you left E*TRADE, you transitioned to the Civil War Trust. How did that came about?

As I hinted before, my days at AOL and E*TRDE were fantastic but I could tell it was taking a big toll. My time at AOL and E*TRADE had put me in a good financial position and I felt like I was at a point where I could consider other passions. I wanted to stay in the online space but didn’t know exactly in what capacity. From my very earliest days, I’ve loved history. When I came back to the DC in the Navy, I was excited by being surrounded by so many historical monuments. I had supported this outfit called the Civil War Trust which upkeeps and preserves Civil War battlefields. They were a highly motivated and talented group of people but they had one of the worst websites you could find. I thought they would be in a much better place if they re-did their website. I made that pitch to them and I think it caught them off guard. But I convinced them that I was sincere. I thought it would be for a year or two but that ended up being a much longer gig and I’m grateful for it because it totally re-energized me. It gave me the chance to dabble into web platforms and capabilities that in a large corporation, I would have never had the opportunity to touch. We were able to grow online fundraising and public awareness though the website updates.


That’s great because it seems like that was a real passion project for you. What advice would you give someone surrounding to what degree they should aim to work for something they’re passionate about?

I guess it depends where your passion lies. If you’re passionate about bitcoin or cryptocurrency, that’s going to be easy to lineup a job and your passion. But for me it was a little different. When I was at AOL and E*TRADE, I was passionate about what I was doing. They kept me very interested. But there became a very practical side too where I was compensated very well. And without those successes, I may never have indulged in this transfer to the Civil War Trust which proved to be a really important step for me.

I think you could stunt yourself if you just go after your passion without thinking of what kind of career that will ultimately be. But you can stunt yourself going the other way too. So it’s probably somewhere in the middle – a mixture of the two.


Can you share with us how you moved on to Mount Vernon after being at the Civil War Trust?

After the Civil War Trust, I had established myself more in a non-profit capacity and I was asked if I would be interested in doing something similar for George Washington’s Mount Vernon. Mount Vernon had built a tremendous reputation but was really backwards in terms of technology. So it was really fun taking my skills from the Civil War Trust and applying it to Mount Vernon. I was the first person at the organization to hold the title of Vice President of New Media. So it was another tremendous period of creativity. Eventually I was asked to take on other responsibilities and my current title is Senior Vice President of Visitor Engagement. I oversee our welcoming programs for our over one million visitors per year and I also oversee our marketing team that work towards promote the organization and educate our visitors.


Do you have any advice for military members about methods for figuring out what job or career might be right for them?

It’s a great question and I’m not sure I have the exact answer. For me, I got really lucky in leaving the military and going into a field that allowed me to continue through my career. However, there’s so much online about every industry so if you’re interested in a particular industry, I would encourage you to find any information you can as well as reaching out to people in those industries to learn more.


Are there any resources you would recommend to veterans?

I recommend the book called Shoe Dog by Phil Knight, the founder of Nike. He talks about how your life and career won’t be as linear as you think so you really just try to enjoy the ride. The tenacity in that book was really empowering. Particularly for people looking to be entrepreneurs, it’s a great read.


What are some common misconceptions military members have about what life will be like in the civilian sector?

I think there’s a stereotype out there of military people as disciplined and motivated. However what I found is that there are civilians that are just as disciplined, motivated, and hard working. So I learned how to hold my colleagues in high regard and be humble. Just because you were in the military doesn’t mean you have a monopoly on these skills.


That’s great. It reminds me of Episode #33 with Brit Yonge. He said, “It’s not like while we were in the military, everyone was sitting around playing Lincoln Logs.” I think it’s definitely helpful to take the mindset that the civilians you’ll be applying against are just as hardworking as you are. Is there anything else that you think veterans will need to overcome in order to find success in their career after the military?

For younger folks, I think it’s about learning to speak the right speak. For those getting out later, there is a certain expectation that you have a certain business wherewithal. In this case, an MBA might be more important in that transition.


Is there anything else you’d like to share that we haven’t covered?

It’s been a long time since I served in the Navy. Today I really appreciate the opportunity I had to serve in the military. People have been really happy to hear my military stories and I have been happy to hear theirs. You’ll be able to connect quickly and easily with other veterans on the business side. That service will serve you for years to come. And If you’re thinking about moving on to the civilian world, it’s definitely doable even if doesn’t end up being a completely linear path.


Those are great parting words of wisdom. I very much appreciate your time today, Rob.