How to transition form the corporate world to the startup life - Ryan Geist Interview
Today I interviewed Ryan Geist who is a good friend of mine that I actually met online. He talks in full detail about how he made the transition from the corporate world to the startup life. He was a consultant at Deloitte Consulting for 3 years before making the leap into the entrepreneurial world, so his experiences are very relevant to those of you who are sitting in your cubicle dreaming about starting your own company.
Contact: Ryan [at] RyanGeist.com
[Download the audio of the interview available at the bottom of this post]
To the minute summary of the interview:
1:08 - What did you love and what did you hate about the corporate world?
Ryan loved:
- The expense account and travel
- The comradery and team focused culture
- The training and learning involved with a big company
- Mentorship available from managers and team leaders
Ryan did not like:
- The lack of freedom; his creativity was crushed constantly
- His growth was stunted
- He saw smart people at Deloitte, but he didn’t want to be like them
2:33 - How did you stay focused on becoming an entrepreneur and not get sucked into the corporate lifestyle?
Ryan set a time bomb for himself when he started Deloitte. As soon as he walked in, he told EVERYONE that he was planning to work at Deloitte for a couple of years and then leave to do his own thing.
3:55 - Were there any drawbacks to setting the time bomb?
There sure were drawbacks. It’s a great way to keep yourself honest to your true goals; however, it will stunt your growth in the company and you will hit a glass ceiling because the company doesn’t want to promote you. You basically make a name for yourself that you’re not here at the company for the long-term, so the company doesn’t want to invest a promotion on you.
5:14 - What were the differences between the corporate company you left and the startup company you joined?
In the corporate company, the environment was extremely structured and a lot of times Ryan would be doing “bitch” work because you have to pay your dues in an entry level position. Ryan went from grunt work to all of a sudden being the leader of a company where he was responsible for overall vision, direction, and strategy.
Ryan loved the ability to be creative and really work on the things that he was passionate about. He didn’t like the lack of structure because it was like he was completely on his own with no one to guide him to the best practices and decisions for the company.
6:47 - What could you have done different with Razume to have given it a better chance of succeeding?
The number 1 reason Razume didn’t succeed was because of the team. There were too many people “advising” the team, and the developer and designer left right before they joined Launch Box Digital.
8:22 - What could you have done differently to keep the team together or create a better team?
- No one has a side job
- All the founders have the same amount of equity
- The team lives together
9:21 - What advice would you give professionals who are currently in the corporate world and want to leave to start their own company?
- Try to start your business as a side project
- Get traction before you leave
- Make a lateral movement to a job that gives you more time to work on your startup company
- Make sure you have your team established before you leave
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Download audio of Ryan Geist Interview (Right click to download)






Interesting interview. I’m in a similar position, but I was *forced* out of the corporate consulting world recently. So far its been going well, and I’m glad to be doing my own thing, so hopefully my project will get off the ground and get some traffic! I just have to follow some of Ryan’s tips!
@Liz - I am so happy that you’re doing your own thing and that your projects will lift off soon. Ryan definitely has some really good advice and you should reach out to him just to chat.
What does xelango do?
This is great! I loved it. Great questions for anyone thinking about making the jump from corporate to startup.
@Jun Loayza - xelago is a recommendation engine for things to do in the city. Right now it is only based in Boston, but I hope to expand to other cities soon.
Its a bit of a cross between Netflix and Yelp. Feel free to check it out! It is not totally interactive unless you rate things that you have done in Boston.
Hey Jun,
Great post and great interview with Ryan. Ryan thanks for sharing all that valuable info. I think it means a lot to people to hear first hand from someone that has worked at a top consulting firm that it doesn’t compare to being on your own.
Tony (Web 2.0 Expo 2008)
Your signature rocks Tony.
Will miss you at this Web 2.0 09!