Jake Cusack, managing partner, CrossBoundary

1. What was your first job?

I started a homemade granola business when I was just seven. Although the cereal tasted good it didn’t look that nice and so the business didn’t last too long. So you can say my first venture failed.

2. What parts of your job keep you awake at night?

I think about the safety of our employees when they are in dangerous spots. I think about the long-term outlook of the business. I also think a lot about recruiting and how to identify and hire the best people. We have a very rigorous recruiting process and diligently listen to references because we feel talent is the most important thing to our business.

3. Who has had the biggest impact on your career and why?

My parents showed me that it’s great to accomplish things whether in business or sports but that it’s not the most important thing at the end of the day. That is a valuable perspective, both when things are going really well and going really badly. As long as you still have your family and your relationships things will be okay. They also taught me to be humble. Many of my opportunities have not been due to me. They arose because I was lucky to have the parents I had, the education I had, the fortune to come back safely from military service in Iraq, and to receive scholarships to a top school. I may have earned 5% of that myself – but 95% was a blessing from my parents and God.

4. What is the best professional advice you’ve ever received?

During my first tour to Iraq I was really eager to prove myself and have the experience of combat so I sought out risky missions. Then my commanding officer sat me down and told me I wasn’t going to find that satisfaction on a battlefield. I did not believe him at the time but later understood he was right. You can go accomplish whatever you think you want, be it money, a certain experience or prestige – but it won’t provide full satisfaction. So while it’s good to be ambitious, happiness won’t necessarily come from achieving all those goals. You will never be satisfied by some external accomplishment. That’s not the answer.

5. The top reasons why you have been successful in business?

I think I am willing to take risks both in the physical and financial sense. I am able to see opportunity where others might see risk. I think I am pretty curious about different things so do a lot of research and ask questions – which can be a good trait in business.

6. Where’s the best place to prepare for leadership? Business school or on the job?

I was lucky to have both. The military taught me a number of leadership lessons while I was young. It taught me what to aspire to, the importance of leading by example, and the discipline to sit down and think through what could go wrong. How to strip away the unessential elements and think about the core objective. And business school was really helpful because I did not have a business background. It transformed me and gave me that skill set quickly. It helped establishing credibility in a new space.

7. How do you relax?

I like outdoor sports such as skiing, hiking and climbing. The countries we work in have fascinating adventures to offer, so when possible I plan a weekend of exploring. Unfortunately most of my time during work trips revolves around meeting rooms. But wherever I am, I like to run in the city because it is an interesting way to learn a place both quickly and from a different perspective.

8. By what time in the morning do you like to be at your desk?

I travel almost every week so it really varies depending on jet lag and the other schedules I’m coordinating with. My times are not consistent.

9. Your favourite job interview question?

I like to ask candidates about when they were wrong about something, and then when they were right but everyone else thought they were wrong. When did you know you had made the right decision about something when everybody else thought the opposite? The answers to that often help show how the candidate reacts if they are passionate about something but no one else is. How do they convince other people? Are they confrontational or collaborative – both of course can be appropriate, depending on the context.

10. What is your message to Africa’s aspiring business leaders and entrepreneurs?

I think there are businesses that might appear somewhat boring from the outside, but they really need great talent. Due to the hype around technology there is a temptation for young people to work on the sexiest new technology. But there are basic fundamental businesses in education, healthcare, consumer products and energy that really need to be run well in Africa.

There are massive opportunities in those businesses. They are not as appealing as technology but hold opportunities that can provide meaningful change in a society. Similarly, I think working in finance has gotten a bad name in the west, but in these markets you can clearly see the value it offers.

Lowering the cost of capital can make a previously expensive item accessible to poor customers. For example, increasing access to electricity and lowering the cost of energy for small business. Bringing accountable private investment into a market can create jobs, and make market incentives for companies and governments to reform and follow international best practices. And ultimately strengthen the institutions in a country by providing tax revenues and accountability.

Second, if you are an African diaspora, or a foreigner thinking about working in Africa, just go. Don’t necessarily try to find the perfect job from the outside. As soon as you arrive you will find many opportunities and have a better sense of the market. So be willing to take that risk.

Jake Cusack is co-founder and managing partner of CrossBoundary, an investment advisory firm focused on conflict zones and frontier markets in Africa, Asia and the Middle East. CrossBoundary works with local entrepreneurs, investors and policy makers, helping them do business in unconventional markets. Prior to starting CrossBoundary, Cusack worked for emerging markets private equity firm Abraaj.