Advice for Transitioning from Wall Street to Start-ups

In my last post, I talked about some the challenges and barriers to success facing Wall Streeters interested in the start-up world. Difficult doesn’t mean impossible – it just means that you are going to need the same passion, intensity, steely resolve and thirst for learning for transitioning from Wall Street as you’ll need for either founding or working in a start-up. So it is actually a pretty healthy and necessary self-selection process, in my opinion. Over the last 4+ years I’ve done stuff that I couldn’t have imagined that made all the difference in my acclimation to the start-up/technology world. The thing that will be difficult for most Wall Street refugees to understand is that being at a technology start-up, whatever your capacity, isn’t a job: it’s a way of life. Because success is partly dependent upon being an active learner, opening both your mind and your heart to new and non-intuitive things on a daily basis.

While I am only one data point, I will share some of the steps I took to make the transition from Wall Street to Silicon Alley, and continue to make every day.

• Reach out to friends who either work in or are investors in start-ups. Duh, obvious, right? One of the guiding principles on Wall Street is using data to make decisions, and it should be no different when making this transition. You need to speak to lots and lots of people who have either gone through what you are contemplating, or who have experience with those who have attempted the same. I was lucky to have guys like Fred Wilson and Jeff Stewart as early resources, both as data points and as connectors to others who gave me even more data. While your experience, personality and skill sets are unique, those of others can be very, very instructive.

• Immerse yourself in the start-up ecosystem. This means going to relevant Meetups, presentations offered by law and accounting firms, select conferences, etc. Subscribe to Gary’sGuide.org and other meeting notification services in order to keep your finger on the pulse of the technology and start-up scene. See, be seen, collect business cards from both investors and entrepreneurs, and hand out zillions yourself. Eventually you will become a fixture in the community. And this is a good thing.

• Become a “Let’s go out for breakfast” and a “Let’s grab a coffee” madman. Network, network, network. Entrepreneurs. Venture capitalists. Angels. Potential clients. Potential partners. Smart people in your domain of interest. These meetings exhibit exponential – not linear – benefits upon your networking and data collection process, as people in this realm tend to be incredibly helpful and introduce you to lots of other people who become nodes – offering new connections – themselves. Once you get this ramped up your learning absolutely skyrockets, and the contacts you make can help land a job, locate a business partner or de-risk a new venture through an advisory or commercial relationship.

• Read lots of good blogs. There is so much great content out there, stuff that seems like it is written JUST for you given your areas of interest. Take advantage of this. It is also a great way to meet people with common interests with whom you can start a dialogue, out of which might come – who knows? I’ve commented on people’s blogs, sent them emails and built dialogues that evolved into great relationships. Becoming an avid consumer of the medium is very important from both knowledge and networking perspectives but also for getting your head around being a start-up guy.

• Start a blog yourself. I know, it’s not for everyone. But if you fancy yourself a start-uppy kind of person, then you must have the ideas necessary to populate a blog. The value, however, is well beyond that. It is a place you can refer people for greater insight into you both as a person and as a professional. It is a platform for igniting conversations around topics of interest to you. And it brings with it a certain aura of engagement, of caring enough to set it up and maintain it. This is pretty important cred when interacting with technology types, many of whom have blogs and use them to great effect. While it takes a meaningful amount of time to do a blog and do it well, it is a valuable mechanism for getting fully ingrained into the technology ecosystem.

• Join and use Twitter, Facebook and LinkedIn. While I’ve been on LinkedIn a long time, I find myself spending the most time on Twitter, followed by Facebook. LinkedIn is a distant third. While I think it is important to have a presence on all three, Twitter is clearly the most dynamic, fastest moving, and most powerful vehicle for getting a grip on the conversations happening in your areas of interest. Twitter and blogs. Choose the Twitterers and bloggers you follow well and it will pay off in spades. You will be extremely well-informed, on the cutting edge of information, and have a circle of influencers with whom to interact. It’s all good.

• Separate – really separate – from Wall Street. It is really, really hard to sever the spiritual umbilical cord. The political machinations that were irritating while you were on the inside are a compelling soap opera once you go outside. Resist the Siren’s Song. Also, it can make the fear even greater when you stay close to people still on the (albeit smaller) gravy train while you’ve made the break. Don’t hang out with them. Spend the time getting acclimated to your new world. This doesn’t mean saying goodbye to friends; it just means having a clear delineation between personal and professional boundaries, and refusing to allow yourself to live in the past. Making the break is hard. Once you’ve done it, DO IT. Don’t let yourself get sucked back in. Because you will end up depressed and frustrated, and further way from your goal of being a different kind of person, a different kind of professional. You deserve better. Move on.

• If you can, do a little angel investing and/or advising start-ups. I am strongly against “dabbling” in the angel investing domain, but I view this as a little pocket money akin to going to Vegas or AC to play poker. Becoming an angel, getting to see how others start companies, pitch ideas, interact with investors and staff their firms is invaluable education, well worth the price of admission. I’m not suggesting spending a material amount of your net worth doing this, but enough so you are able to see some deal flow and perhaps use a more experienced friend to help select a few small-ticket investments. Also, putting yourself out there as a potential adviser to start-ups is a great way to learn about how they work. With your domain expertise from Wall Street, you could add a lot of value to a nascent company. Get engaged. Help out. And learn, learn, learn.

• Acknowledge the challenges but don’t be daunted. If you come into this transition with humility, excitement, intensity and focus, you can make it happen. Invariably the road will contain some potholes (if my own experience is any guide), but persistence is what makes great entrepreneurs and great partners, and what makes victory at the end of the day just so sweet.

Don’t worry, be happy? Not at all. There is plenty to worry about. But there is a lot that you, former Wall Streeter, can do to make your move into the world of start-ups a much more satisfying and successful experience. Best of luck and get on with it.