Should startups cash in early or stay on?

By Dennis Clemente

So if you’re a startup, would you rather cash in early or stay on for the traditional 7-years long cycle to profits before cashing out? Which one makes more sense?

For those who are thinking of a quick exit, lawyer Roman Fichman had the following to say after hearing from a five-man roundtable panel of executives from a cross-section of verticals who spoke about how they pick founders, define startups, prepare for acquisitions and exits, and predict the hot trends.

• Founders get cash quickly
• Because there aren’t too many investors at that point, founders get a larger percentage which translates to higher dollars per year of work, in contrast to having continued on a longer path and collected investors along the way
• They get an exit notch on their belt which is important if they intend to start up a new company
• Bird is on hand versus who knows what the market is going to be like in 7+ years?
• Smaller deals can be done quicker and cheaper
• Founder relations haven’t had the time to sour yet, i.e., one can remain friends with fellow founders

Either way, it should encourage anyone to start a, well, startup if you’re not there yet and for those in there, to think how you can stay long enough to learn more, as we did with the panel of speakers consisting of Anand Sanwal, CEO/co-founder of CB Insights; Barry Silbert, founder and CEO of SecondMarket; Ben Boissevain, founder of Bois Capital, Ed Zimmerman, venture lawyer and tech chair of Lowenstein Sandler and Wiley Cerilli, VP of Constant Contact. They all made for an interesting mix of proselytizing speakers, pragmatic ones and even slightly controversial ones.

“I want people to leave their safe jobs,” said Ed Zimmerman last September 11 at the Enterprise Tech Meetup at the Midtown office of Lowenstein Sandler where he is the tech chair.

The point Zimmerman was trying to make was how our jobs don’t guarantee us a golden parachute but which is possible in the tech world. “Can you get a $200 million exit strategy from you jobs?”

But if you did listen to him, how would he go about choosing you? For Zimmerman, it’s all about charisma and what he thinks is almost impossible to find. “Unfortunately, technical talent and charisma don’t always come in one package,” he said. This makes a technical co-founder vital in a startup.

Zimmerman represents start-ups and growth companies in raising money, selling the company or cashing out, and depending on market conditions, considering public offering.

Zimmerman has angel invested in more than 30 companies and invested as an LP in several venture funds. One of his VC clients called the companies Ed likes to help “tinkertoy internet companies” (as opposed to heavy core tech and drug discovery companies) and that suits Ed fine. Digital media, e-commerce, social media, fin tech, SaaS, cloud/virtualization, enterprise software and adtech are, apparently, all tinkertoys. Ed also founded First Growth Venture Network for startups which doesn’t charge or take equity, GrabArborVC, AngelVine VC, and the charity HoopAPaluza.

Once you have a startup in place, Cerilli said you will need to find out where you in your startup phase and in the process figure out, “Are you in the family, tribe or organization?” phase. Cerilli clearly knows what he is talking about, having been in two startups, Single Platform which was acquired for $100 million in 2012, and Seamless Web.

In front of all these VCs and executives, the obvious question is, how do you know when you need to raise money? “The time to raise capital is when you have a perfect storm of an idea,” Zimmerman said. “You have a great idea? Get enough money to survive till seed (funding) stage.”

Boissevain added how important it is to “get funded right away” and iterate like a “rocket ship before big companies” catch up on you.

And once you get the funding, Silbert said it’s important to stay focused.

How do you know if your company is doing well early? Sanwal said if startups can hit the milestone, good. If it pivots all the time, there’s a problem. Silbert cautioned, though, how companies do a lot of zigzagging and should always be aware of not “misinterpreting it.”

In terms of recruiting talent, Zimmerman said he keeps a wish list of founders and tech talents, even if I don’t have a business in mind yet. Having done a lot recruiting, Sanwal said he always felt pressure when hiring. “We hire the wrong person and recruiters are just useless.”

The meetup was moderated by Deirdre Bolton, an anchor on Bloomberg Television and host of the alternative assets show “MoneyMoves,” airing weekdays at 1 p.m. ET, across Bloomberg’s digital platforms, including Bloomberg Television and

The Enterprise Tech Meetup, the only community-run network of support for technology startups driving innovation in the enterprise, brings together large corporations, entrepreneurs, investors and others to help grow the next generation of influential startups in NYC.

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Dennis Clemente

Shuttling between New York and other US cities, Dennis writes about tech meetups when he's not too busy working as a Web Developer/Producer + UX Writer and Digital Marketer.

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