So, What’s My Next Move?

I've reached another career and personal inflection point. It's not about moving on. (Because frankly, I enjoy it here. A lot.) Instead, it's about branching out.

Frequent ChannelE2E and MSSP Alert readers know that I've been in and around the IT media market since 1992. The journey has included a healthy mix of successes and failures at big, midsize and small IT media companies.

The biggest career successes have involved working with my longtime business partner, Amy Katz. During a previous chapter in our careers, we co-launched, built and sold a few media brands (2008-2014). Then we took some time off, and returned to launch After Nines Inc. -- which provided the springboard for ChannelE2E (2015) and MSSP Alert (2017).

Fast forward to present day, and ChannelE2E is the biggest IT media site we've ever built -- growing quarter-over-quarter (every quarter) since launch. Meanwhile, MSSP Alert is our fastest-growing media property to date. And yes, it has also grown quarter-over-quarter (every quarter) since launch. We're enjoying the journey. And we can't thank you and our sponsors enough for your readership, feedback and guidance.

But where do I go from here? The short answer involves doubling down on what I know and love -- blogging for ChannelE2E and MSSP Alert. But there's also another interest that I can't ignore. It involves the angel investor scene.

Step One: Explore, Fail, Learn

As a journalist, I've covered mergers, acquisitions, venture capital, startups and exits pretty much since I graduated from college. I've dabbled in "traditional" investments (stocks, bonds, mutual funds, ETFs, etc.). I've invested in my own businesses, and partnered with Amy Katz to bootstrap our current company and a previous business.

But... I've never opened my wallet to pump money into a third-party startup. Until recently, that is. My journey toward angel investing started around 2014. Amy and I had just exited our previous business. I took a few months off. I explored the angel investor scene in my own back yard, here on Long Island. I found some impressive accelerators and incubators such as Launchpad Long Island.

But I found the Long Island tech scene far too fragmented with no clear central hub of activity. Many of the "service providers" at various angel meetings here on Long Island are lawyers, bankers and M&A consultants -- rather than angels and entrepreneurs seeking funding. Certainly, everyone should be welcome in the room. But the room needed more brides and grooms rather than caterers for the occasion, if you catch my drift.

By mid-2014 and 2015 I turned my attention to Manhattan. Once again, I explored various angel investor groups, incubators and accelerators. Former Intronis CEO Sam Gutmann (who now leads OwnBackup) introduced me to Golden Seeds, an angel group that only invests in women-owned startups. I was impressed. Really impressed.

The Golden Seeds membership and leadership are packed with business veterans who largely built their fortunes in and around Wall Street and financial services. Those leaders always welcomed me to meetings, discussions and due diligence conversations. But I was a minor leaguer among major league financial all stars.

I also made some mistakes. Looking back, I spoke far too often and listened far too infrequently. Surrounded by all that knowledge in the Golden Seeds room, I should have sat back and soaked up a whole lot more of their investing know-how. My other challenges: Golden Seeds investments often involved non-tech companies. Meanwhile, I'm tech-obsessed. And my bank account doesn't exactly measure up to Wall Street's heavy hitters.

Step Two: Double Down on What I Know

As Amy Katz and I began to ramp up ChannelE2E in late 2015 and early 2016, I stepped away from Golden Seeds. As we scaled this media site, we saw multiple worlds converge -- MSPs, private equity, software startups, seed funding.

With ChannelE2E, we were once again at the right place at the right time. Based purely on demographics (mainly, the age of MSP and IT service provider business owners) we knew a massive merger, acquisition and exit wave was coming. Additional factors (recurring revenues, cloud services and private equity) intensified the M&A and investor trends.

We've long tracked the small business shift toward outsourced MSP relationships. At some point, Amy Katz and I realized the trend would repeat itself in the security market. Our thesis was simple:

In other words, we firmly believed those small business owners would eventually need to outsource cybersecurity to MSPs and MSSPs. Hence, our MSSP Alert site launched in May 2017. Again: Right place, right time.

Step Three: Skate to Where My Own Puck Is Going

Amid my IT media journey this past decade, some of my relatives moved from New York to Florida -- not far from Orlando. My wife and started to visit those relatives quite frequently. I also spent considerable time at Orlando-area IT conventions. Plus, Tampa-based tech companies like ConnectWise had my attention when I was in town.

By late 2018 or so, I had my next epiphany: Instead of exploring the angel investor scene in New York and Long Island, I should skate to where my own puck was heading -- Florida. I searched. I Googled. I researched  some more. And I discovered Florida Funders -- a hybrid venture capital-angel investor organization.

On the one hand, Florida Funders runs a venture capital fund that invests in early-stage, Florida-based technology companies. (Confession: Venture capital funds are too rich for my blood.) On the other hand, the organization offers a crowd-funding platform for angel investors. Among the benefits: Florida Funders manages all the due diligence and deal valuations. Then the platform presents those deals as potential investments to angels (and aspiring angels like me).

I like the approach. A lot. I mentioned it to my wife. She was intrigued.

But could she and I trust Florida Funders and its management team? At first glance, the core team has world-class tech and investment credentials. But my wife and I wanted to do our homework and really understand the organization's leaders. When we took a closer look and poked around, our confidence grew stronger.

The reason? Some of my most trusted sources in Florida (such as former ConnectWise CEO Arnie Bellini and former ConnectWise Director of Business Development Gerwai Todd) spoke highly of the Florida Funders team and their track record in the tech market.

My wife and I realize angel investments can lose money. Our bigger concern was making sure we were preparing to invest through an ethical organization, with ethical leaders. Conversations with longstanding sources we trust gave us peace of mind.

By January 2019, I became a Florida Funders member.

Step Four: Listen, Learn, Invest

As I mentioned earlier, I spent too much time talking during my first attempt at angel investing (2014-2015). This time around, I spent far more time listening, studying business plans, and poking around for potential investments.

The journey involved a Tampa visit to Florida Funders' offices in February 2019. (Ironically, that visit occurred the same week I stopped by ConnectWise to investigate a potential company sale...)

My Tampa trip included a sit-down with Florida Funders Director of Business Development Saxon Baum. Sharp guy. I learned about the various investment options for members. I quizzed him about the organization's direction. I felt at home in their offices. Frankly I wanted to learn more, and I wanted to engage. So I did.

My most recent steps? The first one involves my first angel investment, which occurred via Florida Funders a few weeks ago. The second step involves another trip to Florida in late April for... stay tuned.

So What's Next?

In the days ahead, perhaps I'll:

Special Thanks: In the meantime, special thanks to my wife for putting up with me as I continually adjust how I spend my days. To my business partner Amy Katz for building the IT media platforms upon which I stand. To industry peers like Sam Gutmann and Gerwai Todd for showing me the ropes in the angel market. To new peers like Saxon Baum for opening new doors for me. And to organizations like Golden Seeds and Florida Funders for your efforts to empower entrepreneurs who want to build lasting, diverse, inclusive and innovative businesses.

Count me in.