entrepreneurs

Dear Entrepreneurs, Here’s Why We’re All In

I have always loved angel investing. There is a great sense of pride in being able to say that you identified the potential in an idea or an entrepreneur early on. Then there is nothing more rewarding than watching a company grow, hire new talent, solve customer problems and invest in its community. Because companies are run by people, it’s even more immensely gratifying to see founders and team members execute towards goals and achieve their grand ambition.

Community and legacy are two of my strongest motivators and so I always knew that I would want to make angel investing a larger part of my life. But, over the last few months, as I decided to make investing a full-time gig, I knew I was going to have to do it differently. 

I knew that simply writing checks and sending the entrepreneurs on their way was not going to be enough. I am simply not wired to be passive. If I am going to be involved in something then I am in. 

All in. 

I have been fortunate enough to surround myself with people at York IE who have the same mindset. None of us have ever wished for success. We are the type of people who roll up our sleeves and get to work. The team is hand selected. Me to them and them to me. We’re forever intertwined.

Which is why our approach to investing is so hands-on. Our philosophy is that today, capital isn’t enough. There is a lot of money out there – more money than ever. Getting money isn’t the hard part. 

The hard part is executing, operating, growing and scaling.

Young Kyle
A young Kyle, hustling

As an entrepreneur, anyone can give you money. Only someone who has successfully grown and scaled a startup can give you advice and guidance on how to do that. Unfortunately, this is not how boardrooms and venture capital work. I don’t know the exact numbers, but I’d argue over 75% of investors have never spent one minute building a company of their own. Through hard work – and maybe a little bit of luck – my team and I have done this – to tremendous heights. More than once.

Yet we’re also humble enough to realize that every company, every founding team, and every market is unique and different. There is no one-size fits all template. Anyone who tells you that there is a playbook, over-analyzes your SaaS KPIs, or drives you that you “must go up-market to enterprise” certainly hasn’t walked a day in your shoes. That’s why an investment team needs to provide unique value to each investment. At York IE, we selectively invest in companies we feel we can help accelerate.  

If you’re an entrepreneur reading this, let me talk to you directly for a moment: Hands-on doesn’t mean micro-managing, but you need to want the coaching. You know how to run a great business. I have seen small founding teams accomplish more and with greater innovation than enterprises 10X their size and even 1000X there size in my most recent experience. People who work at startups are bad ass. That’s why I love working with them. But even with that Herculean effort, no one can do it all. And, honestly, there are things you don’t want to do. 

We pledge to help.

We will focus on the things you’re not passionate about or don’t have as a core competency. This will unburden you to double down on your strengths, which will help speed up your growth. And, listen, I know very well you will not need our help forever. As you continue to grow, you’ll be able to hire in-house folks with these specific skill sets. That’s the whole point! We want to be an extension of your team in the early days helping you get to the point where you don’t need us as much any more. 

(Ok, now back to talking to everyone!)

Of course, that type of relationship requires trust. Our goal is to become more than just another investor. I think my friend, Rami Essaid, founder of Distil Networks, which was acquired by Imperva, said it best when I asked him for an endorsement.

“Kyle is one of the most responsive advisors I have had the pleasure of working with. He has always come through with thoughtful and helpful answers and has become one of the first calls I make when I have a question.”

Thank you, Rami!

And to think, I was that responsive when I was doing investment on the side, as a small fraction of my time. Imagine the commitment I can give my entrepreneurs now that this is my job and I have a talented team and infrastructure alongside me. 

We always want to be an entrepreneur’s first call. 

It doesn’t matter the topic or the time. From questions on fundraising or go to market or sales comp or competitors or industry trends or product roadmaps to introductions to other investors or a new head of sales, call us. We will answer. 

Between me and the rest of my team, we have seen a lot of things. And we’re keeping our skills sharp (more on that in another blog). So we’re still learning and experimenting and, most likely, failing, which is going to teach us even more. 

It all comes down to our definition of investment. We believe to truly help a startup, we need to invest more than money. We need to invest time, sweat, knowledge and maybe even a little blood. 

Because we’re investing in more than just an idea we think will be profitable. We’re investing in the future. We’re investing in the entrepreneurs themselves. We want to transfer as much knowledge out of our heads into theirs as we can. Because we believe in them. We believe they are the types of founders and executives who will invest in their own businesses and grow them to become companies that nurture talent and impact their local communities. 

We’re not investing for fast exits. We’re investing to build wealth. Wealth is more than money. It is all about legacy. 

We want our legacy to be that we got our hands dirty and along the way helped the next generation of great entrepreneurs and startups.

Growth. Delivered.

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