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“Never take a job for what you earn… (angel investing the employee way)”


Back in 2002, I was attending a conference where author and educator Robert Kiyosaki was speaking about entrepreneurship and investing. He said, “Never take a job for what you can earn; take a job for what you can learn.”

Learning on the job could be the secret to success for Wei Gao, a former Amazon executive who was once Jeff Bezos’ shadow. Gao recently joined London-based online events startup Hopin as its chief operating officer.

While at Amazon, Gao’s 16-year tenure included a number of senior positions, including vice president of grocery tech, product, and supply chain and technical advisor to Bezos.  She follows in the footsteps of Hopin’s former COO, Andy Jassy, who now is CEO of Amazon after Bezos turned the mega-company over in July.

Success stories abound with people who start at entry-level positions. Great leaders don’t always start on the executive team, though Wei Gao technically didn’t start at entry-level either; she started as a senior software developer straight out of earning her masters at the University of North Carolina at Chapel Hill. [Source: LinkedIn]

Starting at the Bottom

General Motors CEO Mary T Barra started out on the assembly line at General Motors inspecting hoods and fenders.

Wal-Mart CEO Doug McMillon loaded trucks at a Wal-Mart distribution center as a teen, earning $6.50 an hour so that he could earn his college money, but rose through the ranks as an assistant store manager and buyer in merchandising.

Chris Rondeau started out working at the front desk for his local Planet Fitness and is now at the helm as CEO of Planet Fitness.

Michael Corbat started out in sales of a bank owned by CitiGroup, rising through the ranks to CEO of Citi’s global wealth management and head of global corporate before being named as CEO of Citigroup in 2012.

Samuel Allen started out at John Deere as an industrial engineer in 1975. His path up the ranks included becoming president of worldwide construction and forest division, before being named CEO for John Deere and chairman of the board in 2009. [source: Business Insider]

A personal mentor, Heip was destined for med school by his parents who escaped with their children from the Vietnam crisis when Hiep was a child. However, when he wasn’t successful with some of the subjects in school, he went to work as a customer service rep for a payment processing company. He worked his way up the ranks and within 10 years was running the company when it was purchased by another payment processing company. He was then asked to run that company before he retired in 2016.

Working for a Startup

What should you expect when you take a lower compensation in exchange for a share of the company when it goes public? What questions should you be asking in the interview before you accept an offer? What should you know about yourself? What other questions would you want to ask before you or your child goes to work for a startup? What do you do if you find you’re working for a company that is behaving badly?

Risk Tolerance and Tolerance for Change

Startups inherently have risks. I’ve worked for several and started my own a couple of times. They have a high failure rate. Plus, if you’ve experienced and been comfortable with walking into an organization that has an easy onboarding process where you have a clearly defined job description that they expect new hires to be plug-and-play workers, and you liked that, you probably won’t enjoy working for a startup. Startups are inventing their working processes. In many cases, there’s a steep learning curve for the founders. It’s chaos. Rolling with the punches and taking on the attitude of “see a problem; fix the problem” will help you do your part to build a company that you’re investing in every day.

It can’t be an attitude of “it’s just a job” when you have a stake in the gains if the company is successful.

Investor Mindset on the Job

Some days you might find yourself in the mailroom, or making coffee, or helping the shipping department, or answering customer service calls. “It’s not my job” should never cross your mind. If you’re always thinking WIFM (what’s in it for me), working at a startup is probably not for you.

Your financial success as an angel investor is directly influenced by how well everybody does. And that starts with you. Most angels only get to invest with their money. But when you get into an on-the-job type of angel investment, you’re investing with your skills, your time, your ability to influence necessary changes and growth in the company, you’re in a very powerful position. You cannot think like an everyday employee as you work!

There Is No “I” In Team

Most startup founders are brilliant and hire for the gaps in their knowledge and experience, as well as the day-in-day-out workload to be accomplished to get things done and product out the door. You’re part of a team, where you are all in – skills, ideas, and effort.

And as new people come on board, it can be easy to become resentful, because you might have been putting in the sweat and extra hours for months only to have a newcomer who has loads of experience and skills come in telling you what to do.

Consider that this type of newcomer might have been completely inaccessible in a large company. I had the experience of being mentored by Hiep, who I mentioned above. Never in a million years would I have been able to talk with him, ask him questions and learn from him, had I not met him on one of those startups. The same with Papa Bear who I’ve talked about in a couple of Angel Insights emails I’ve sent to you. I’ve been blessed to know some incredible people by working for startups.

Hiep especially focused on core values in his most recent startup – what he wanted to have his company represent and the attitude of the team he brought in to lead: those core values included integrity, innovation, love, humility, and service. There really wasn’t a place for the narcissistic ego-driven celebrity-personality behavior that sometimes highly successful individuals might bring to a team along with their very desirable skills. Hiep filtered for his governing values in the people he brought on and they have, in their own right, been great mentors and friends!

The Come and Go of Things

One startup that I was privileged to work for was actually fairly mature in its evolution. Company meetings routinely went over financials, sales, returns, and pipeline so that we could see where the company was in meeting targets, and how much debt the company was carrying compared to profits.

All around the office, there were perks like an honor-system breakroom and a breakroom manager who kept it stocked with coffee, Crio Bru, pita-chip+spinach dip cups, yogurt, boiled eggs, and veggies+ranch dip, as well as the regular chips and snacks you’d expect in company vending machines. Some employees I talked with, grumbled about what was missing though – where the company had cut budgets and perks to put toward more infrastructure and better health insurance benefits.

It had me thinking back to my own first startup – the lunches I brought in while we were working on a deliverable, the tickets to Disneyland for an employee and his wife who were willing to drive a rush delivery to a customer in Thousand Oaks, California, and how lunches went away to upgrade the phone system and move into a bigger building.

The theme here is change. There’s a lot of it and change comes in many forms.

Bottom Line: Evaluating the Risks

When you’re being asked or you are offering to work for less in order to have a stake in the gains the company makes, you’re taking a significant risk.

Your best safeguard is to ask questions before you take on these risks. The interview process is a great place to have those candid conversations before you step in and commit. Some of your questions might require you to sign a non-compete. And in fact, consider that a non-compete requirement might also protect you from other potential hires gaining more proprietary information than suitable for a person who doesn’t actually join the team.

Here are some of the questions you might ask:

How will you be able to evaluate the progress of the company?

How transparent are the founders? Are they as transparent as the mature startup I mentioned above?

Are questions encouraged?

Are ideas and solutions encouraged?

What’s the 5-year plan?

Which questions would you like answered before you accept an offer to work at a startup?

Bottom line

While you may end up working for a startup that fails, and you lose your entire angel investment as that employee, you will never regret what you learn. And if you follow Robert Kiyosaki’s insights, you could find yourself with a wealth of knowledge that you can take to the top wherever you end up!