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“I quit J.P. Morgan for an Amazon internship. People said it was a big mistake, but helped me launch a new career”

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Kiri Masters of Bobsled Marketing

Friends thought I was making a mistake, perhaps a really big one. I had a great title, an awesome salary, top-notch benefits and clients who I enjoyed working with. But, I was leaving it all for an as-yet-unproven career as an entrepreneur. Some wondered whether I had I gone crazy.

Beginnings in the Land Down Under

My career started out with a marketing internship in Sydney with Australia’s largest bank, The Commonwealth Bank.

I was fast-tracked in a management-development program where I chose different disciplines every six months, ultimately landing with an internal consulting group that solved big organizational problems that would otherwise be farmed out to consultants. I also partnered on a project with a team from McKinsey.

“If I can make it there…”

In 2011, my husband and I moved to New York City, where JPMorgan Chase hired me as a vice president and strategy manager. Not bad for an early 20-something, if I do say so myself.

A couple of years in, I transitioned into a client-facing banker role. As a business banker, my client book was mostly based in Brooklyn, where I got a full dose of tech startups and much older, multi-generational businesses. I got pretty good at deciphering the financials and creditworthiness of seven- and eight-figure companies that were either in real trouble or about to blast off.

The siren call of entrepreneurship

But, I had somehow caught the entrepreneurial bug. I spent hours absorbing everything I could find on launching a startup, even listening to podcasts on my daily subway commute. I wanted my own shop, where I wasn’t constrained by an inability to simply do the right thing, often buried in processes, procedures and layers of management.

I started an ecommerce site. And it did grow, but it was taking forever to find any notable traction. My side hustle finally started to take off when I launched my products on Amazon.

I also saw other brands who were struggling to get off the ground with Amazon. I knew that I had the chops, but I needed to show more before people were going to hand me money to help them to be successful with Amazon.

This was the beginning of my “mistake.”

No looking back

With no guarantees that my plan would work, I quit the bank and took an unpaid apprenticeship with a very successful Amazon consultant, with the clear understanding that I would soon become an Amazon consultant myself. I was proving that my strategies worked with my mentor’s clients while starting to land my own.

Early in my internship, I noticed that a lot of crowd-funded companies needed help setting their products up for sale on Amazon, and I could quickly build a sales wireframe that would take these startups to five-figure monthly sales. It was time for me to leave the roost and go it alone.

Lessons learned

Today, only 12 months after leaving JPMorgan Chase, I lead a team of five who have successfully launched over 100 products for 20 companies. We’ve grown sales for everything from pillows and drones to toys and beer posters. We’ve successfully driven products who received Shark Tank investments, too.

At this one-year milestone, I took a little time to reflect and consider what I have learned. Here are my five lessons:

  1. Be an “intrapreneur” first
    • You might secretly hate your banking job, but there’s a lot you can learn from inside the comfy confines of a bank – and that steady paycheck buys you time and resources. Find any way you can to get close to the “smaller” clients. I learned so much from my experiences with the smaller clients, because they were what I aspired to be.
    • Don’t be afraid to suggest improvements. Sales skills are a must if you’re going to strike out on your own, and pitching a client is much less scary than pitching your boss. Test a thesis you have and build supporting data. You might get rejected, but you might not, and you’ll learn a lot regardless.
  2. Build relationships
    • In banking, you are literally surrounded by the best of the best. Network more than you think that you should. Attend company events. Find ways to help other people without expecting anything in return. The difference between startup success and failure can often be measured in the size of the founder’s network.
    • I’ve gotten client referrals from past coworkers with physical product clients and these provided the early foundation for Bobsled Marketing.
  3. Look for apprenticeships
    • I’m not advocating a position where everyone should go all kamikaze, quit their jobs and work for free. There are a million learning opportunities all around you. Volunteer to apply your skills to a small non-profit. Study the masters of sales, marketing, startups and entrepreneurship. Get involved in forums such as Quora and begin building your “brand” long before you take that “see you later” walk towards your manager’s office.
  4. Love the things that banking beats into you
    • There’s nothing sexy about staring at another profit and loss (P&L) statement or sitting through some boring sales meetings, but consider how many businesses you actually get to review. Those are real-world, sink-or-swim businesses with tangible successes and actual problems.
    • The more that you commit to pushing past the boredom and digging into all of that data, the more developed your eye for the little details will become. You’ll notice something that’s headed for a five- or six-figure mistake and head it off at the pass.
  5. Start now
    • As I look back, my first ecommerce business was really tough sledding. But, if I didn’t start it, then I wouldn’t have learned everything I now know. Crashing and burning with a side business has a much softer landing than when your next mortgage payment isn’t depending on its success.

Looking back at that pivotal moment in my career, I’m so glad that I made that “mistake.”

Kiri Masters is the founder of Bobsled Marketing and a former VP and relationship manager at JPMorgan Chase.

Photo courtesy of the author

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