An Angel's Perspective: Tony Wilkins

Hi 👋 Welcome to the Angel Insights newsletter from VITALIZE.

Each month, we feature angel investor interviews to give you unique perspectives, tips, and strategies on early stage angel investing. Share with a friend who may want to subscribe and learn about angel deals.

This edition spotlights Tony Wilkins, a veteran angel investor with a track record spanning over two decades. He likes to do 3-4 deals per year, focusing on globally scalable, disruptive, and efficient digital businesses led by outstanding founders.

How did you become an angel investor?

In my 20’s, I had a specific financial goal in mind and realized that salary, savings, and investing in the stock market wouldn’t get me there. Knowing that companies like Apple and Microsoft (I call them intelligent lottery tickets) back in the mid ‘80’s got started by small teams of brilliant entrepreneurs, I began backing founders I thought had incredible potential to generate outsized returns.

What is your favorite thing about being an angel investor?

Introducing founders to contacts that move the needle on their financial and personal growth.

What is one lesson you've learned as an angel?

I’ll never be expert enough to know which businesses will succeed, but I have become increasingly expert enough to know which people will succeed.

Any advice you would give to a new angel investor?

Don’t do deals you don’t love!!

What is the most important part of your diligence process and why?

Assessing the integrity, chemistry, coachability, resourcefulness, resilience and responsiveness of the founders before I write the check. Why? There will be tough times in the lifecycle of even the most successful companies. The people running those companies - not the tech, financing, marketplace or competitors - will solve them. Though it sounds cheesy, it’s true that tough times don’t last, tough people do. You have to be tough to successfully give birth to a new company and see it through to an exit. People forget about the end goal and whether the founders can get there.

Any adjustments you've made after angel investing for awhile that made a difference?

Ugh! Still making them:

Saying “no” more frequently and decisively.

I often say I’ve made more money on the deals I’ve passed on than the ones I invested in. Saying no has helped me avoid a lot more losses than the ones I’ve sustained over my career. I’m working on passing even more frequently so that I have powder and bandwidth to focus on the deals and founders I love.

What do you think the future of angel investing will look like?

More crowdfunding for non-accredited investors and more syndicated deals for accredited investors.

What else do you think new angels should know, if anything?

Two things.

1. Have a specific goal for your investing journey, and formally check your progress against it at least annually.

2. You can’t learn how to swim without getting wet. You can’t learn how to be an angel investor without writing a check. Go on Wefunder, fund a friend’s business or invest in an angel network right away. Your sophistication will improve with each experience.

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Thanks for reading, and I hope you’ve been inspired today! 🙂

Peace, love, and angel checks,
GaleforceVC