(Big Disclaimer: This page is long and
probably boring. Read at your own risk).
Like many investors, I started out as an entrepreneur. “Serial entrepreneur” to use the trendy term. I founded roughly a dozen small businesses, all bootstrapped. I was in the trenches day-in and day-out, frequently working on multiple projects at once, probably just like many of you reading this.
Everything from SaaS, ecommerce shops, my community, health products, and my long-standing search marketing agency. I’m not going to lie, entrepreneurship can be really damn hard, and can go from extreme bliss to complete exhaustion and back all in a matter of hours.
And I loved almost every minute of it.
Over the many years of grinding hard, learning from my mistakes, and from the guidance of others, my entrepreneurial skills slowly improved. I got fairly good at getting traction on projects and executing quickly. As some of the projects continued growing far bigger than I ever expected, I wound up being lucky enough to have some take-off, leading to a couple of sizable exits.
Post-exits, I did what most do, I became “an investor” (insert eye-roll here). I allocated capital to just about every type of investment out there. Dozens of angel investments in traditional high-risk high-reward startups, an LP in half a dozen funds, dabbled in public equities, private debt deals, real estate, and last but not least… started buying online businesses in their entirety to add to my growing portfolio. I was in search of “my thing”. A type of investing that I could latch on and pour my professional soul into, something that provided great returns, but also something that felt right.
So, guess which one I decided to double down on?
None of them.
There is nothing wrong with any of the above types of investing, but they just aren’t right for me.
Angel investing is a lot of fun and makes you feel cool, but seeing 8 out of 10 companies go bust from throwing profitability out the window in the search for maybe-billions just doesn’t fit with what I want to do all the time. Add to that a decade of illiquidity and stressed-out founders and I’m just not the man for it. It’s not wrong (plenty get very rich), some of my angel investments have been quite successful, it’s just not really what I want to spend all my time doing.
VC doesn’t align with how my brain works, and also I’m still not convinced that it’s a good investment overall, especially once you consider the downsides and required luck-factor.
Public equities have their appeal, but shoving my head in financials all day and being so far removed from the business just doesn’t tick the “winning at life” box for me. Also, what are the chances I could even beat the returns of an index fund? (slim)
And lastly, buying entire online businesses was the greatest teacher of all. It seems great in theory – I’m an experienced marketer who knows how to grow companies quickly. What’s not to love about acquiring some to do just that?
Unfortunately it doesn’t really work that way in practice. I’m good at getting traction, spotting opportunities, and quickly executing ideas. I’m pretty much horrible at absolutely everything else. “Managing” an existing project that is already 90% done is just about the worst productive thing that I can do with my time.
So, what’s the point of spilling to you my entire life story?
To let you know that I DID find what I needed to be doing, and who I wanted to it with. It is now what Smash is dedicated to.
I built Smash to be the type of partner, investor and possible mentor that I wished had existed for me earlier in my career. My life would probably be much different if it had.
See, I look back on my biggest financial success thus far. It was a SaaS company in the ecommerce space. My co-founder and I knew that we had something special. This thing was a rocket-ship of growth and users loved us.
The problem we had, is we were so incredibly scared that something would happen, and it would go to zero. How dumb would I look? We were also complete n00bs to the SaaS space and didn’t know what we didn’t know.
This is why I wish something like SmashVC had existed. If we could have brought on a partner to help guide us and to give us a partial exit, giving us some extra padding in our personal bank accounts, we would have been able to sleep better and continue building the business to its full potential. No matter what, we would have came out ahead. Instead, we were scared, and we exited way too early leaving FAR too much money on the table.
Smash is designed to be an answer to that problem
At Smash, we partner with existing profit-focused businesses in order to either:
1. Help acquisition-focused entrepreneurs get access to capital
I love the ETA (entrepreneurship through acquisition) SMB scene. It’s doing good for our world (allowing founders to retire or move on), it’s helping entrepreneurs ramp up quicker, and it provides good returns for us.
Self funded search funds and SBA loan acquisitions are perfect partners for Smash.
2. Give founders the option for a partial exit.
For entrepreneurs who already own a business, this option might be for them.
Instead of wondering if they should grow it or sell it, founders should have the option to only sell a portion of the company. To take some chips off the table, and keep the upside of continued growth. I’m open to buying anything from 5% to 50% of a business.
3. Literally do the work to help your company grow.
When I invest, I come with a world-class SEO agency at my side to help your business reach the next level. Those who co-invest with me on each deal all have unique mastery-level skills of their own, from techies, to ad specialists, to systems and outsourcing pros. We come ready to get our hands dirty.
Interested to connect?
Want to discuss a potential partnership?
Let's have a chat to get to know each other.