Career Switch: Transitioning from Finance/Consulting into Startups
I’ve had quite a number of requests for advice on how to transition from a career in finance/management consulting into tech startups, so I’m sharing a blog post I wrote a while ago for a career transition site called Careerosity, for others who may be going through a similar transition (with slight modifications). Please note that since this was posted in Oct 2012, some information may be outdated (e.g. my current position). But for the most part, the core message stays the same. It’s also interesting to reread this as it resonates surprisingly well with my recent speech at TEDxKL Women (I had not reflected on this post while writing my speech but clearly, my thoughts were seeded over a year ago).
Last but not least, I’ve added some new notes below about how to break into startups as a non-technical person, if you’re not planning to start one yourself. Hope it helps!
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From Management Consulting to being a Tech Entrepreneur
Posted Oct 2012 on Careerosity. Year of career transition: 2010
- What do you do now, and what did you do before?
I am now the founder and CEO of a tech startup called Reclip.It (www.reclipit.com) in the Bay Area. Before I started my company over two years ago, I was a management consultant in NYC.
- So, why the change?
2008-2010 weren’t great years to be in management consulting in NYC, when most of our clients were in financial services. In college, I wanted to be a consultant to learn about various types of businesses and industries really quickly and to help large corporations solve difficult problems. But rather than working on the more exciting “market expansion” or strategy-type projects, we turned to outsourcing, procurement, and cost-cutting projects as the economy demanded it. My job was miserable to say the least, and I was seeking change. I’ve always been entrepreneurial my whole life and even started my first business when I was 9 years old. I’ve always left a small sliver of something that I’ve started – almost like a legacy – in any organization that I’ve been a part of, and I figured that I’m meant to eventually blaze a trail and start my own thing. When I was exploring options for what to do, I discovered tech and was quickly drawn to it. So, I set out to immerse myself in the startup world.
- How did you pitch yourself to the desired industry/role?
When I wanted to quit management consulting, I didn’t immediately think about starting a tech company. A friend encouraged me to evaluate areas that I’m passionate about and devise ways to get more involved in those sectors to learn more about them. I was really passionate about food, fashion, and travel back then, so I decided to pick one: food, and delved into that industry.
I tried interviewing with TastingTable for an ad ops intern position that would eventually lead to a FT pay of $20K/year (a massive pay cut from my consulting gig although I didn’t mind it at the time because I was passionate about getting into the food industry). Unfortunately, they felt I was “overqualified” for the position and didn’t offer me the internship. Then, I started a food blog and did a short stint as a restaurant critic for CitySearch. I even enrolled in the French Culinary Institute to master gourmet cooking skills. When I learned more about the food biz, I realized that starting a restaurant was one of the toughest businesses ever (high risk, high capital, high turnover, long hours), and decided against it.
Then I turned to fashion. I thought about my own problems with clothes and tried to solve it. My first ever tech startup idea was to build a “virtual fashion closet,” and I initiated it with 2 short-lived business partners. I wrote a 40-page “static” business plan and sent it to a mentor, who immediately told me to throw it out of the window and buy Steve Blank’s book, “The Four Steps to Epiphany” to understand how to quickly test and validate ideas & assumptions, as a path to building a scalable web business. He also referred me to read Eric Ries’ blog and (more importantly) Paul Graham’s essays. I quickly adopted those principles and realized that the fashion idea was too ambitious and complex; it would simply not work. I also realized that if I wanted to start a tech company, I would need to iterate quickly and needed a “tech co-founder.” I was lucky that a former college-mate of mine, Jhony, who was working at IBM as a developer at the time, was also thinking about starting his own company. I was able to recruit him to be my co-founder to start working on what we considered a small side project in the daily deal space, while still on our full-time jobs. And I could’ve never imagined the whirlwind journey we went on shortly after.
- What was the most valuable thing you did to prepare for the new industry/role?
I’d say that the best thing that happened to me during my career transition was to have a few really amazing mentors who were willing to point me toward the right direction and were readily available to answer any questions I had. Granted, I was also very eager to learn and did everything I could to immerse myself in something that was entirely new to me (programming, web designing, site analytics, attending tech events, seeking out the right “traction role models,” reading up resources online, attending the Lean Startup Machine Weekend, alpha- and beta-testing various new websites and apps, getting to know other founders, etc). I think a big part to any career transition is how motivated and dedicated you are to the new industry, once you’ve identified it. Another thing that helped was being accepted into an accelerator. As first-time entrepreneurs, it gave Jhony and I the initial seed investment and conviction that this could turn into a bigger idea than we originally thought.
In hindsight, rather than jumping right into starting my own company without prior experience, it might have served me better to start out interning or working at an early or mid stage startup to learn the ropes. Having never started a company before, I made a ton of inevitable, rookie mistakes. Working at a startup initially will expose you to the rawness of a small company and will help when you start running yours.
- What other advice do you have for readers seeking the same career change?
With the glamorization of startups by the media like the Social Network and TechCrunch, a lot of people these days have a somewhat distorted perception that starting a company is fun, glamorous, respectable, etc. But I always ask those who are thinking about starting a company if they’ve had a history of being 1) resourceful, 2) an extreme risk-taker, and 3) generally an optimist. Have you tried to hack something in life? Have you taken huge risks in life or done something outside your comfort zone? Have you ever started something on your own? It could be a club in college. A lemonade stand. Do you always think about what could go wrong, or do you imagine what the possibilities are?
Some people dive into startups as if they were a bucket list item on their resumes, but they’re doing it for the wrong reasons. Anyone who’s considering a startup should figure out their underlying motivation for transitioning into the new career. As I was considering a career in the food industry, a good friend (an actress in NYC) cautioned me that my passions (something that I enjoy doing leisurely; i.e. cooking, scotch tasting, dining out, food photography) may not be something that I would enjoy doing professionally. It’s actually really important to understand the consequences of making your passion your profession. For example, you may be really passionate about playing the guitar, and being a musician could be really rewarding and satisfying, but it comes with a price – sacrificing a stable income, living with uncertainty, etc. So make sure you address the roots of why you’re switching careers and if possible, try to dabble into those fields before blindly diving into it.
Last but not least, here’s a story that forever changed my perspective on trying to figure out “what I should do in life.” After college, I attended an alumni event where a businessman spoke about how he became really successful in his career. At the end of his speech, I went up to him and asked “Sir, the particular space that you’re in sounds really niche. How did you know that this was what you were passionate about and what you wanted to do in life??” to which he answered: “Young lady, I can tell you this for sure. You will never really know exactly what you want to do in life. Some find it sooner, some later in life. I’m in my 50s and I still don’t know what I want to do in my life. But what I do know is what I DON’T want to do. And as long as you keep trying different things and don’t settle on things that don’t make you happy, you’ll get closer to what you eventually DO want to do.” That night, I felt a huge burden lifted off my shoulders; the pressures of having to “follow my passion” and to “figure life out,” was no longer weighing down on me. I realized that all I had to do is to view life as a series of trials and errors. Just as a startup is “a corporation set up in search of a scalable, repeatable business model through experiments and rapid iterations,” you should iterate your life until you find a career that is ideal for you!
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Advice for Joining a Startup if you Don’t Have a Tech Background
- If you’re completely fresh in this area and are trying to figure out what skills you should pick up, I’dadvise you to look into acquiring one of these domains as anexpertise, and then try to get an internship at a startup (post Series A or B) to gain some technical skills:
- UI Design: graphic & visual design skills, design tools (e.g. photoshop, illustrator, etc), best practices & current trends in design (e.g. flat design, responsive design, iOS7, fixed navigation, circular design, infographics, custom font faces, etc), basic html/css, difference between web and mobile
- Product Management: wireframing skills (using balsamiq, omnigraffle, etc), data analytics, conversion funnels, AAAR pirate metrics, presentation skills, SCRUM process, writing product requirements, understand technology, project management, etc
- Marketing Analytics: data analytics (using Google Analytics, Mixpanel, etc), conversion funnels, growth hacking tactics, SEO/SEM, CAC & CLTV calculations, excel, viral mechanisms, social referral programs, etc
- User Experience & Prototyping: prototyping tools (using Axure, InvisionApp, Mockingbird, Cacoo, etc), behavioral psychology, user-centered design, information architecture & hierarchy, perception of overall site map/flow, empathy, user modeling, etc
- User Research & Customer Development: interviewing and surveying skills, behavioral psychology, lean startup methodologies, research techniques and tools (eg. usertesting.com, etc)
- Front-end Coding: HTML5, CSS3, Javascript (jquery, sencha, jquery UI, etc), possibly some database design skills
- If you are more interested in business development, operations or artistic marketing, unfortunately, you’re going to have a lot more competition, especially when there are fewer internships for these position. Unless you have a really incredible network or a lot professional experience in what you do, it’s going to be a tough entry point into startups.
- There’s no one right way to build skills in the domains I’ve mentioned above, as they’re relatively new and aren’t even taught in colleges yet. The good news is that they can all be learned by tackling real-life problems, and by using a lot of web or mobile products. If you’re already at a startup, volunteer to help another team. If you’re transitioning, ask a friend if you can help with his/her website. You’ll intuitively know what’s a good product and what’s bad, so take lots of notes on all the little things you notice.
- If possible, build up an online profile and/or portfolio – this will come in handy when you’re applying for a job. Keep in mind that every employer googles your name before the interview, so make sure you have a decent profile. The top 3 things that should show up should be: a) your linkedin profile, b) your personal website/portfolio, c) your twitter account or some article showcasing your achievement/involvement in an organization that’s legitimate
- Last but not least, here’s a goodie but oldie post by Mark Suster that you should definitely read if you’re thinking about dabbling into startups – Is it Time for You to Earn or to Learn?
Please let me know if you have any other suggestions or feedback! Hope this post will help point aspiring entrepreneurs in the right direction.
Breadcrumbs by Cheryl Yeoh 
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