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Want to succeed as an entrepreneur? Stop job hopping and find your ‘modern MBA’

A field guide to building a career in entrepreneurship without job hopping or grad school

Dylan Serota
Story by
Dylan Serota

Co-founder & Chief Strategy Officer, TerminalDylan found his passion for the future of work and formulated the idea for Terminal at Eventbrite where he spent seven years building teams that spanned Sales, Strategy, and Product - including an eng… (show all) Dylan found his passion for the future of work and formulated the idea for Terminal at Eventbrite where he spent seven years building teams that spanned Sales, Strategy, and Product - including an engineering team of over 100 in Mendoza, Argentina.

dserota

Many of us who are committed to building a career in entrepreneurship have grappled with a perceived tradeoff: keep working or go to business school?

Business school offers connections, education, and fun, but also can come with massive debt and the creeping doubt that it’s unnecessary. The other option — joining the workforce and hustling to the top — can also feel like an arduous journey. The natural inclination for climbing the entrepreneurship ladder is a spin cycle of working a year or two at a company before moving on to a new title and a bigger paycheck. Wash, rinse, repeat.

I’d resigned myself to the job-hopping strategy when I began my career at Eventbrite. Thankfully, a mentor transformed my thinking.

David S. Pottruck is the former CEO of Charles Schwab, and scaled the company from a few hundred employees to tens of thousands. I was incredibly lucky to meet with him after I graduated college, a pivotal point in my early career.

David pointed out that many of his peers had taken a job-hopping post-college path, traveling a vertical line — from junior sales associate to senior sales leader, for example — and topping out in a single discipline. The ceiling is lower for specialists, David noted; there’s only so far up you can go.

To be a successful entrepreneur, David recommended a broader path of experience across as many areas of a company as possible, from sales and marketing to product and customer service. He pointed out that a versatile skill set would be invaluable if I ever needed to run a business unit and that experience would give me a commanding view of all aspects of an organization — setting me up for bigger leadership roles in the long term. If I ever wanted to run something, I’d need that wider skillset and a broad base of experiences. 

I was inspired. Instead of sticking to the playbook of staying at a job just long enough to find that next shiny object and bail — or opting for the questionable and expensive investment in business school — I decided to stick with one company on the upswing and learn everything I could. 

It was one of the best decisions of my life. By pulling back from “next gig” thinking, I built a career path that taught me how to run a company and ultimately fueled my ambition to start my own business. I understood all aspects of an organization and built a real career path, not just a series of jobs.

By doing so, I would set myself up for greater earning potential in my peak years, which is an important tradeoff to consider compared to near-term salary increases that job-hopping provides. Today, I think of this approach as “the Modern MBA” — and it was essential to give me the skills to win investor confidence and build my own company.

Building your Modern MBA

The Modern MBA delivers the full raft of business experiences — and emotions. I’ve tackled hard growth problems, seen firsthand how businesses and cultures evolve, and rode out the inevitable ups and downs of a scaling startup. I know how companies work inside and out, from getting the accounting right to pushing through engineering problems to resolving thorny customer issues. Many of us move on when there’s a downturn or problem outside of our expertise; in the Modern MBA, you dig in and solve them.

Start by picking a company. Your company will become your school, your learning platform, your Modern MBA alma mater. While you can’t predict the future, bet on a startup on a sizable growth trajectory, which creates more surface area for you to cover. Next, look for a product that excites you.

I had a background in the music space and used Eventbrite as a concert promoter; their self-service tools were far easier to use than the agony of exporting Ticketmaster data into Excel. I knew there was a massive opportunity. Add in strong backers and a seasoned executive team, and it was as good a bet as you can make.

Next, prove your value and build social currency. I started in sales, paying my dues doing the East Coast grind from California, arriving in the office by 6AM for a brutal day of cold-calling. I got rejected, a lot. But I listened, upped my game, and learned. The art of the slow sale, the magic of charming persistence, the right questions to ask, and when to shut up. The grind paid off and within the first year, I was promoted, then shortly after promoted again and had the opportunity to lead a team in my mid-20s.

When your heart stirs — and it always does for the entrepreneurial-minded — make your move internally. With a track record of results and a reputation for overcoming setbacks, I had enough “OG respect” that when I proposed moving into API strategy, they let me. While I didn’t know much about APIs, I cornered friends, spent long hours at the office, dug into the classic tome “APIs for Dummies” and leaned hard on our VP of strategy. Good things happened, and soon I was running the platform. 

I completed my Modern MBA at Eventbrite in seven years — unheard of in Silicon Valley time. Armed with that experience, I’ve since co-founded a company and have had the fortunate opportunity to advise on several more.

It’s not just a job — it’s an education 

When undertaking the Modern MBA, it’s important to recast work as not just a job but more so an education. I looked for people smarter than me to take me under their wing. I didn’t just get things done, but also strive to learn the underlying theories behind day-to-day practices. And I solicited feedback at every turn, even when it was ugly.

I recommend starting in sales. Sales is transferable to any business and imparts critical lessons around listening to customer problems, taking feedback to heart and overcoming objections. It’s also humbling and character-building — as I learned the hard way — and that’s vital for running any business.

There will always be the allure of fresh challenges at new companies. Recruiters will call, friends will pester, larger salaries will loom.  One day your interest in your current work will likely dwindle and you’ll feel an urge to jump, to pull ahead in the race in your head with others from your college class.

Take the long view — think in career decades, not job quarters. Title inflation is rampant at startups; you’re seeking long-term monetizable skills, not a fluffy director title that won’t mean much in a few years or a short-term salary bump. 

Assuming your company’s still growing fast, spend the social currency you’ve accrued to create a new, exciting role within the company where you can master new skills and round out your understanding of the business. Companies don’t want to lose great people and most will work with you to expand your horizons and skillset. (And if they don’t — you may not want to work there after all.) 

The Modern MBA is the best education I’ve had. While there were many lessons along the way, the biggest is that the greatest growth often comes from staying put.

Published October 11, 2019 — 11:00 UTC