The Money Column

Whew. This week was like a tornado. Tons of meetings, conference calls, closing some investments, monetizing others and then the Money:Tech conference. Where to start...

Money:Tech 2008

First, the conference. Tim O'Reilly's brainchild, hosted and facilitated in grand fashion by Paul Kedrosky, the conference brought together an eclectic group of people from the spheres of investment management, technology, entrepreneurship, venture capital and media. This human mash-up made for a series of very interesting dialogs, both inside and outside the formal sessions. I was proud and thankful to have been asked pretty early on to chip in my ideas about the conference, possible speakers, etc., and hopefully I ended up helping out Paul a little bit, at least. Paul wrote a nice post while on an airplane summarizing his thoughts on the conference, and you should take a look. I'd also like to thank the friends who were on my panel including Stewart Alsop of Alsop Louie Partners (who gave me a bunch of crap; it was great), Bruce Golden of Accel (way too nice to be a such a good VC, no?), Cary Davis of Warburg Pincus (who gave Paul a lot of crap; it was great) and Salil Deshpande of Bay Partners (an amalgam of nice, giving crap and a VC; a potent mix). In any event, a worthwhile expenditure of time. Thanks to all who participated.

Money and Mytrade

Next, it was announced that one of my portfolio investments for which I had helped run the deal and sat on the Board was acquired. Mytrade, founded by Andy and Landon Swan, was acquired by Investools after less than half a year. It is a testament to the vision of the founders, the quality of the business model and recognition of the value of integrating a highly flexible, lightweight multimedia consumer platform with brokerage and order execution. Andy wrote an informative post on the birth, growth and sale of Mytrade. Check it out to get more info. Suffice it to say, it was great working with Andy, Lando, Howard Lindzon and Kenny Finkelstein on the deal. Great entrepreneurs and great partners make for great outcomes. I was proud and pleased to be a part of it.

Deploying New Money

During the insanity I also managed to close an investment in Charlie O'Donnell's innovative career discovery start-up Path 101. This is an area I've gotten to know pretty well through my (quite successful) vintage 2004 investment in TheLadders.com. TheLadders was my first early-stage investment - what the hell did I know about online business models having spent the prior 17 years in M&A, derivatives and trading? Not much, I'll tell you. But what I did manage to extract after so many years on Wall Street managing high-performance teams was how to assess talent and how to evaluate business models. Clearly I am not holding my judgment out to be unimpeachable, but time has shown that it's pretty good. And when TheLadders.com founder and CEO Marc Cenedella sat in my office, pulled out a visually bland but highly informative deck and took me through the business, I got it immediately. And I liked Marc a lot. I had been introduced to Marc through a friend, so the personal reference was strong, but his sheer intellect, drive and passion made it easy for me to write a check. Fast-forward to today. I've made 20 investments since that fine day in 2004, co-founded and built a venture-backed financial technology company and have some investment wins under my belt, so I feel somewhat more confident about my ability to pick em'. And in the immortal words of Larry David, I'm feeling pretty, pretty good about Charlie and Path 101. And I'll be right there to support him along the way. Good stuff.

I continue to see fantastic businesses across both financial technology and digital media spectrums and will be putting more money to work shortly. These are very, very exciting times in these spaces. Notwithstanding the economic maladies afflicting those both inside and outside the U.S., early-stage investment opportunities remain both abundant and attractive.

Leveraging Existing Money

I am also actively working with some of my portfolio companies like Buddy Media (which is taking off like a moon-shot) and Clear Asset Management (finding strategic partners to leverage the firm's high-performance algorithms). One of the reasons why I've focused my investments in financial technology and digital media is because they are areas that I understand and where I can add value. But this only works if the entrepreneurs are great and open to input, and in these cases both Mike Lazerow and Andrew Corn fit the bill to a T. It is great to be helpful and to be involved in the growth, development and success of these and the rest of my companies. I am confident that Mike and Andy can make it big and that I can be part of the value-creation equation.

How do I Want to Make Money?

Raise a fund? Run an alternative asset management firm? Coming to terms with my professional identity at this point is challenging. My roots are in Wall Street and hedge fund management but my last 3.5 years have been spent in the worlds of entrepreneurship and investment. I miss the markets, but have become very entrenched in the early-stage community from both entrepreneur deal-flow and venture capital perspectives. I have also become quite wedded to blogging, which has given me a public persona that generally runs counter to Wall Street and asset management's practices of keeping a low, private profile. So I am in the process of figuring it out. It should be a very interesting and exciting 2008.

Comments

[Paul Rubillo]

Roger, everything you told me when we first met one year ago, has turned out to be spot on. You told me it would take 6-9 months to truly flush out my idea with dividend.com. After all the ups and downs of getting the site built, biz models though out and all the stress that comes with "the dream". We are in a good place and building what we hope becomes a financial portal that many new and active investors will come to. On top of that, we were able to launch Putt.com with a great team and that is going really well. Your early appraisal of our passion and grittiness was an ingredient we have always looked back on as a key moment to push forward. Thank you for doing that and I hope you can continue that motivation for others for a long time to come.

[RBH]

You asked (possibly rhetorically) "How do I Want to Make Money?"

Consider this: Is that the right question? Back when I was professing I used to urge my advisees to do what they really really love to do as well as they can, and regard everything else -- money, status, whatever -- as a side effect. It made their parents nervous, but I'll flatter myself that at least some of them are still doing that and are having good lives doing it. Some are making lots of money, some aren't, but they're doing what they love to do and are happy and fulfilled human beings.

[Michael]

Roger -- your thoughts about Marc are very similar to how I felt when I sat down to interview with him (and Andrew ) in April 2004. I really knew nothing, but here we are almost 4 years later. Cool memories...