I’ve made a lot of different kinds of investments in my career, in addition to the “normal” ones like Stocks, Mutual Funds, 401K, 529’s, etc.  I’ve outlined some samples below, but first, a disclaimer – I am not a registered financial adviser and I am neither recommending or suggesting that my investments are suitable for anyone but me.  It’s probably a good idea for you to consult a professional financial adviser before you make any investment.

Myself And My Partners:

The best investments I’ve made so far have been in myself, and my partners, when we started Advanced Waste Services and other businesses.

Advanced was a thing we cobbled together initially, combining savings from our 401K’s, loans from parents, bank debt, etc. with a belief in ourselves, a work ethic and, as my partner Butch used to say, strong backs, which helped us make up for the many mistakes we made.

The return on this investment in ourselves was phenomenal. Not only did we have our equity returned to us several times over during the company’s history, we were also able to create something of great value to us, the marketplace and our team members, from the ‘next to nothing’ with which we started.  

None of my other investments would have been possible

if I hadn’t invested in myself first.

Private Equity:

I was first introduced to Private Equity when we went through a recapitalization process in the late 2000’s. We didn’t end up taking any PE money, but I learned a lot about how PE’s look at and value companies.

I decided to continue that learning process by joining 2 Private Equity funds as a Limited Partner (LP) which is what they call investors. Doing so has given me the chance to buy into more than 15 well-established companies, in a wide range of industries, and be a fly on the wall as to how the deals got structured, financed, closed and operated.

It’s also helped broaden my perspective on how the PE funds deal with fast & slow growth, good & bad management, add-on acquisitions and more. Their goal is to buy a company at Value X – help it improve and build value through better management, product development, acquisition, etc. – and sell it at some point in the future for a higher price – Value Y (and/or higher multiple) than where they bought it. 

Being an LP has made me a better investor and businessman.  I’d encourage you to learn more about Private Equity.  

Early Stage and Angel Investing:

Early Stage – To augment my Private Equity experience, I also joined an Early Stage Venture Capital fund that invests in early, but post-start-up, technology-based companies. They make biggish bets in promising companies that are in the early revenue or pre-revenue stage.

This participation has helped round out my experience as an investor and businessman, exposing me to smart people, interesting companies and complex technologies that I’ll admit I don’t always understand fully, at least at first.  The investments are larger and concentrated in a hand full of companies.  It’s a bet on a lot of risk equating into a lot of reward.  

Angel Investing – After I sold my company, I decided to turn more of my attention to start-ups. I figured that if my most successful investment was my own start-up, paying that forward by backing promising new start-ups as an Angel Investor made economic sense and the exposure to these opportunities would continue my education as an investor and businessman.

At this point, I’ve Angel-Invested in over 50 startups. While the investment in each has been modest but meaningful, it’s been gratifying to be a small part of helping the companies take their business and technology to a new level.

It’s given me exposure to a bunch of new companies and ideas and I feel like that keeps my thinking cool, fresh and active. 

The majority of my investments have been made through Investing Syndicates like:

Phil Nadel’s Forefront Venture Partners on Angel List 

Zach Coelius fund on Angel List 

Jason Calacanis

I’m anxious to do and learn more.  Keep in mind of course that it’s likely that many of these will fail (fingers crossed – only 1 so far), or fall well short of their expectations.

This kind of investing is for what I call “impact” money that I can afford to lose.  

Investment Snapshot:  Below is a sampling of companies and funds that I’ve invested in.  Maybe some might be interesting to you. Podcast Self Management Flexible-Term Co Living The World's Most Personalized Skincare Experience Clothing Built for Life's Every Adventure Flexible framework of housing Robotic Coffee Bars in SF
Capital Midwest Fund Flexible Per Diem Workforce for Healthcare Pain Therapy using non-narcotic treatment
De-Ice is developing electric de-icing for aerospace The Entrepreneurial Operating System Metal 3D Printing Electronic B2B Payments Personalized workout plans - get the app Active wellness at work Healthiest filtered water on the planet Wind Turbine Gearbox Remanufacturing Influencer marketing management solution Real news curated by real humans Robotic Process Automation for Spreadsheets Lawn care services made easy Robot delivery solutions Coffee alternative natural energy Analytics and targeting based on spending Augmented Reality Camera App Proven expedited lending strategies Reflux relief that works Fast, objective road assessments Accounting and financial services for VC backed startups World's best dance classes online at home Invests in small and mid-sized companies Coffee and teas infused with vitamins and superfoods Invests in Wisconsin early-stage companies Long Term Private Equity Investors

Want to hear perspectives from the people in Private Equity, Venture Capital and Early Stage Investing. Listen to one of these podcasts below: