You Have a Career Blind Spot — Ross Baird explains how to fix that (an interview)

Most people don’t love their jobs. Even when the work is interesting and challenging, the majority of people still wonder: Does my job actually make an impact? It turns out that most of us have a blind spot in our career choices. So after reading the newly published book, “The Innovation Blind Spot”, I chased down the author, Ross Baird, for a discussion about how lessons from his book apply to people looking to find purpose and make a positive impact in their careers.

This is my favorite book of the year. Period. (Seriously, go get your copy!). Filled with stories, myth-busting data, and first-hand experiences, Ross takes the reader on an adventure to explain why our “startup economy” is falling short of its audacious claims (much like so many of our careers):

  • The number of startups are actually going down. Roughly three-fourths of venture capital in the United States goes to three states.
  • Only 3% of funded startups are owned by women or minorities.
  • Of 150 “unicorn” companies today (valued at over $1 billion), only 15 percent focused on the six industries that people rely on to live healthy and productive lives (health, food, agriculture, energy, financial services, housing). Venture capitalists are more likely to fund an “Uber for weed” than a service to help curb rising healthcare costs.

All the while, only one-third of employees are actually engaged in their work. Simply put, most startups, as well as many careers, are not making the world a better place. But they can.

While the book is geared towards — and a MUST READ for — entrepreneurs, business educators, and investors, the lessons in it apply to how we think about our careers. I sat down with Ross to talk about how the lessons in his book directly relate to the way we choose our own professions and I hope you enjoy the discussion as much as I did:

Two-Pocket Careers

Mark Horoszowski: You talk about the way people normally separate business and charity: get as much money as you can in one pocket, then give some money away from the other pocket. Your solution is “one-pocket thinking”. While you’re not the first person to talk about this (Slavoj Zizek has a powerful explainer and Anand Giridharadas' talk went viral), but you made it real for investors. Do people think about their careers the same way?

Ross Baird: There’s a lot of evidence that young people today are becoming one-pocket thinkers more and more. A Deloitte study last year showed that only one out of five millennials would be happy working in a place that didn't have a set mission. I attended U.Va and now teach a class on impact investing, which is full of students that want to merge profit and purpose: that class didn’t exist when I was in school, partly because the demand back then wasn’t nearly as strong as it is today.

Riding Unicorns

MH: You highlight how investors love to fund big ideas: they are more likely to invest millions in a moonshot than $50,000 in a validated social good business. I feel like people are the same… they flock to work at “unicorn” companies like Uber or Amazon, even when they are known as stressful places to work. Meanwhile, smaller organizations, unable to compete on paycheck size, even though offering a much more fulfilling place to work, are left staring down the deep, dark “talent gap”. Are people making the same mistakes with their careers that investors are making with their investments?

RB: I’m a big believer, particularly early in your career, that “small is beautiful.” When I got out of school, many of my friends went to McKinsey, Google, or Goldman Sachs, and while they got great benefits and worked with talented people, they had very little responsibility to create their own paths.

Sometimes small can mean the size of the firm. My first job out of graduate school was with a small “one-pocket” investment firm, Gray Ghost Ventures, that was a pioneer in the impact investment field: investing in for-profit companies that had a mission beyond financial returns. My title was literally “Hurricane Chaser,” with a job description of going to find new companies. In practice, I did everything from trip planning to writing agendas to cold-emailing new partnership contacts.

I had a blast. I worked with a great team and while I had to learn on the job (teaching myself finance through reading books like Brad Feld’s Venture Deals and corporate finance textbooks), I had an unforgettable learning and growth experience. When I co-founded Village Capital, it was my experience doing just about everything with a small, meaningful firm that helped me start and build my own organization.

And sometimes small can mean place. I teach at U.Va and the students of mine that are often the happiest right out of school are not the ones that go to New York and get lost in the hustle; they’re ones who go to places like Baltimore, Birmingham, and Kansas City. Cities across the country need leadership, and if you go to a place when you’re young that is small enough to be a community, you can get far more experience than at the lowest rung in a big bureaucracy.

Career Blind Spots

MH: At the MovingWorlds Institute and Impact Teams, we see many high-performing professionals looking to integrate purpose and impact into careers. What creates blind spots for investors, and what can we all learn from that in our professional lives?

RB: The blind spots I focus on in the book all have one thing in common: they are the result of short-cuts, short-sightedness, and lazy thinking. Humans are creatures of habit; we follow patterns, often without even noticing. For investors, that might mean only investing in a certain kind of company (or founder), because that’s what everyone else does. In our professional lives, that might mean only getting information from one news source, or seeking out perspective from people who already agree with you, whether you’re talking work or politics.

On a broader level, lots of the solutions in the book have to do with “bottom-up innovation”: Lifting up the voices of the marginalized (or just the lower rungs of an organization) and learning from their lived experience. My favorite example comes from Adam Grant, who writes about how in the circus, performers are actually better judges of which circus acts will be popular than the circus managers, because the performers are out there every day, actually performing for people. Those who are closer to the problem at hand have valuable lived experience — and as a manager (or investor) you’re missing out if you’re not listening to that experience.

Type 1 Errors vs. Type 2 Errors in Career Paths

MH: I love the idea of breaking apart the errors we make into Type 1 and Type 2. What do you think is the ancillary to our career paths?

RB: When we make bad decisions, they fall into what logic experts call “type 1 errors” and “type 2 errors.” A type 1 error is when you make a bad decision: for instance, if I had the chance to invest in AOL in 1987 and turned it down. Often, the bigger problem is the type 2 error, which happens not when you make a bad decision, but when you fail to consider an option entirely. If I assumed there were no good startups in the Washington, DC area in 1987, I wouldn’t have even been looking for an AOL.

Type 1 errors are problematic, but at least we make them consciously. Type 2 errors are interesting because we don’t know that we’re making them — we don’t know what we don’t know!

OK, so how can we avoid type 2 errors? For investors, I recommend changing the way you screen for startups — rather than just looking for founders with a certain type of resume, start looking for founders with certain character traits like grit and ability to work well with a team.

For professionals, the same thing can apply to hiring. Think about how you screen for candidates, and what unconscious bias might play a role there. The Kapor Center for Social Impact has some very practical ideas for how to do this.

One-Pocket Thinking

MH: Moving beyond two-pocket thinking, you propose “one-pocket thinking” for investors. How can professionals use “one-pocket thinking” to advance their careers?

RB: First, I’d say that there’s a lot that you can do from where you are. You may not love your job in a big institution. Nearly every day, I receive an e-mail from someone looking for a job or for advice about their career. Often these emails come from people who already have a good-paying job but feel stifled or discouraged. They say, “I’m working at an investment bank, making good money, but I hate my job” or “I’ve built good skills at my consulting firm but don’t care about what I do every day. I’d love to work at a firm like Village Capital that has meaning.”

Very often, these people are one-pocket thinkers stuck in a two-pocket job. I typically have two responses.

  1. First, do what you can from where you can. Employees in big companies have time and skills that can help solve one-pocket problems. If you work at a hedge fund or an investment firm, you can work on pricing long-term social and environmental risk of investment opportunities so people can be better one-pocket investors. If you work at a bank, you can help small businesses learn how to get financing: they may be your customer one day. The list goes on.
  2. Second, think about the long game. When you gain experience in a big company, you may be able to start your own one day. One example is my co-founder, Victoria Fram. She knew upon graduating college that she wanted to pursue a one-pocket investing career, but at that time, such firms did not exist. She worked on Wall Street for half a decade to learn how to professionally manage money, and we joined forces after she did a stint at the “Mission Investing” arm of the Gates Foundation.

It’s not who you know, it’s who you get to know

MH: Everybody knows that your networks social and professional are the most important things in your life. Yet we spend so little time intentionally investing in these networks. One thing I hear all the time is “Well, I don’t have a way to contact that person”. In the book, you talk about how Bob Patillo and Steve Case got creative to put themselves in front of a wide array of entrepreneurs. How can we do the same with our networking?

RB: For people interested in working in socially meaningful startups or impact investment firms, the onramp for finding these jobs and getting involved in this network can be confusing — but there are a few emerging programs that demystifying the process.

First off, I obviously recommend the MovingWorlds Institute as a first step. You are doing such amazing work in helping people find careers that are meaningful to them. (MH: Thanks, Ross!)

For people right out of school, starter fellowship programs such as Frontier Market Scouts, at the Middlebury Institute, and the IDEX Fellowship provide a great onramp for your first job. For underrepresented people of color, the Kapor Center fellowship is a very useful onramp. For mid-career professionals, Impact Business Leaders is a great option.

You can also go it on your own, using job boards hosted by groups such as GIIN, NextBillion, or the Aspen Network of Development Entrepreneurs (and more here). Whatever you decide, this is your opportunity to show the world you have more to offer than the leftovers of a successful career. But I’d start with MovingWorlds!

Giving back

MH: Who was a mentor of yours that has made a difference?

RB: In my book, I tell the story about a critical mentor early in my career: Bob Pattillo. Bob was an entrepreneur and philanthropist from my hometown Atlanta. When I first met Bob in 2003, I was 18, and all I really knew about Bob was that he was interested in education, and had a foundation. (I think he only took the meeting because he got a kick out of an 18-year-old cold-calling him). He suggested we meet at Fat Matt’s Rib Shack, and on a sauce-stained napkin, I explained our idea, and asked him for a $10,000 grant. After a barrage of questions, he said, “You don’t need a grant—but I’d do a $10,000 bridge loan.” I said: “That sounds great! I’ll take it! What’s a bridge loan?” Bob said, “Brother, let me take a big step back...” and he gave me a quick tutorial about how finance works over barbecue.

Bob is a raw entrepreneur: the rare person who some people would call “perpetually out of the box”. Bob carries a notebook around that he calls his “inkling pipeline” — different ideas or inklings that could become companies one day. (Bob has about five new inklings daily.) Like a lot of ambitious people in the South, Bob got his start in real estate. But rather than just developing and managing properties, Bob decided to go where other people weren’t. Instead of bidding for big properties in New York and San Francisco, Bob built the next generation of shipping warehouses in places like Louisville and Sacramento, that other people didn’t value. He ended up building the 8th largest industrial real estate company in the country.

At age 38, he was one of the most successful young CEOs in America, but wasn't feeling a purpose. He then learned about an industry called “microfinance,” where investors would make handshake loans to very poor entrepreneurs — mostly women — in emerging markets, and he started to get involved. He traveled the world meeting microfinance clients, and very soon became the largest private microfinance investor in the world. He sold his real estate company to invest fully in “one-pocket” businesses, that both have profit and impact.

What I learned from Bob was three things:

  1. To be successful, you have to work where no one else is looking;
  2. You have to be “all in” — your mission can’t be a side job, it has to be a career; and
  3. You have to invest in the next generation. I wouldn’t be here without people like Bob. I am here because a guy named Bob took a chance on me (He was the one that hired me to be the Hurricane Chaser)! I’m fully aware that, first, everyone who has achieved success has had a Bob; and second, not everyone in life has a Bob. If you’ve been successful, be the Bob for someone else!

Words of wisdom

MH: Any final thoughts or favorite quotes?

RB: Another mentor of mine, Tony Carr at Halloran Philanthropies, always says, “Someday is today!”. Tony has a stable of young folks that he mentors, and whenever they say they’ll get to something “someday,” he reminds them that today is always someday. If you’re reading this interview and have a great idea about a career move —it’s never too late. The best time to take ownership of your career path was when you first started working. The second best time is now.

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