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Clockwork Investor Series

Interview With Kevin Leonard

Kevin Leonard

Name

Kevin Leonard

Fund / Group

MissionOG

Founded

2013

Location

Philadelphia, PA

Number of portfolio companies

21 active

Focus Areas

B2B Fintech, Data, Software

Stage(s)

Expansion stage, Series A to C

HOW AND WHY DID YOU GET STARTED IN PRIVATE INVESTING?

I spent the first 7 years of my career in corporate banking at Wells Fargo, focusing on underwriting credit transactions and managing relationships with a portfolio of Fortune 500 companies. While earning my MBA at Villanova, I took a class on entrepreneurship which piqued my interest in venture investing and the startup ecosystem. I really became passionate about working with disruptive, early-stage companies and CEOs to help accelerate their growth. After graduation, I was fortunate enough to get connected to MissionOG which was investing out of Fund I at the time. It was the right time and place and I haven’t looked back nearly 5 years later.

WHAT IS THE SINGLE MOST IMPORTANT THING YOU VALUE IN AN INVESTMENT OPPORTUNITY?

A strong management team. We want to partner with a CEO/team that has an unique insight on the segment they are disrupting and have built out a complementary team that balances the strengths and weaknesses of the group. While there are many other factors that go into our investment criteria, management is one of the most crucial.

WHAT ARE THE BEST INNOVATION THEMES THAT YOU SEE IN THE MARKET TODAY?

Continued shift in consumer and business payments from paper-based payment methods (cash, check, money order) to digital payments (online, mobile, digital wallet, etc.).

Growing importance of actively managing payments for enterprises – software embedded payments/payment facilitators, payments orchestration and payment fraud management.

Enterprises searching for ways to gain a competitive advantage by harnessing their unstructured data to turn it into smart, actionable insights, and supplementing existing data with external sources.

Growth of governance, risk and compliance (GRC) software solutions as the cost of getting it wrong (financial penalties, reputational and brand damage, competitive repercussions) becomes increasingly more significant for enterprises.

BEYOND ECONOMIC RETURN, WHAT KIND OF IMPACT DO YOU HOPE TO MAKE WITH YOUR PORTFOLIO?

Because operating experience is in our DNA, we understand the challenges and see the opportunities that come with managing high-growth businesses. We partner with companies that are seeking more than just financial capital and who can leverage our platform to create business advantages. Examples of how we work with our companies include assisting with business development introductions, helping to source key talent, identifying potential value-added independent board members, guiding strategic planning and liquidity processes, and brokering introductions to potential acquirers and investors that could serve as the next stage of capital.

WHAT ARE THE MOST PRESSING CHALLENGES OR PAIN POINTS IN MANAGING YOUR DAY-TO-DAY PRIVATE INVESTMENT ACTIVITY?

We continue to evolve how we use data to diligence prospective companies and help support growth in our existing portfolio. While investing can often be more art than science, we are adding as much qualitative rigor to our processes to find, vet, and invest in the best companies to generate exceptional returns for our investors. However, harnessing the myriad data we have access to – from benchmarking studies, company pitch decks, our own portfolio, etc. – is continuing to advance.

Additionally, since the majority of our models, dashboards, tracking sheets, return analysis, etc. live in Excel, we have been finding ways to streamline and simplify our workflows through software solutions.

WHAT IS THE HARDEST INVESTMENT LESSON YOU’VE LEARNED AND/OR THE BIGGEST INVESTMENT MISTAKE YOU’VE MADE?

An important lesson learned has been the more cycles and touchpoints you have with a management team before investing, the better. Since investing can be like a marriage, it’s important to understand the party you will be partnering with, which is difficult to ascertain during an abbreviated diligence period. Strong management teams are vital to navigating companies through rough patches they will inevitably face. An extremely important characteristic for a company CEO is the self-awareness to acknowledge their strengths and weaknesses and surround themselves with complementary individuals. Often where there is smoke, there is fire, and the more interactions you have with a team before making an investment decision often lets negative and positive tendencies and personalities come to light.

WHAT ARE YOUR FAVORITE INDUSTRY INFORMATION SOURCES AND/OR SERVICES?

Pitchbook, PE Hub Wire, a16z, Stratechery by Ben Thompson.

WHAT’S YOUR FAVORITE NON-BUSINESS INTEREST OR HOBBY?

Running

PLEASE LEAVE US A BOOK RECOMMENDATION (BUSINESS OR OTHERWISE).

Endurance: Shackleton’s Incredible Voyage by Alfred Lansing. It’s the incredible story of the 1914 British expedition to cross Antarctica on foot.

WHAT’S YOUR TAKE ON THE PRIVATE MARKET OVERALL?

bearishBearish
bull40tBullish

0

5

10

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