Will Startup Jumpers Hit It Big? Silicon Valley’s Latest Debate Is Portfolio vs Persistence

When gambling on high-risk startups, the more bets you place the better, right? Maybe not.

There is an unspoken discussion going on in Silicon Valley now about the value of “Portfolio” versus “Persistence,” especially among people who have never started a company. The claim is that you can improve the odds of a Facebook-like outcome by jumping from company to company until one hits, building a portfolio of startups (and stock options). I’ve even heard people scheme to switch startups every one or two years, ready to abandon the ship the moment the rain starts.

The alternative is to stick it out and persist through the seeming insurmountable difficulties of building any young company. I think persistence cannot be overrated. But it doesn’t seem to be in vogue.

In the last month, I have been part of discussions with venture capitalists about two super hot startups where the founders are looking to leave. One of them eventually announced a sale for way under capital invested. In both cases the founders wanted to go because they feared missing something big by sticking around another two years or more.

In a more extreme case, an entrepreneur well known in valley circles gave up eight weeks after cashing the final $50K check of a $300K seed round, announcing his decision to take a new job in a text message and burning a number of angels in the process.

I have fallen into the portfolio view, too, though my combination of obsessive tendencies, loyalty and curiosity leads to me to do things like stay on the Spoke board almost 10 years after I co-founded the company. I’ve adopted a portfolio model through a little bit of investing and an agreement to help a few companies.

But it is clear to me you have to be willing to sit through the rain if you want to catch a fish. The value of this kind of founder persistence has been well dissected by a number of successful investors, from Vinod Kholsa to Mark Suster, many a lot smarter than me. In the end, the common theme is that the one solution to bad timing is persistence. Bad timing is the most frequent reason great teams with great ideas fail. The solution is to persist your way through to the point of good timing.

The most important example of this is Steve Jobs. He had a vision for the role of technology in our lives and that vision could not be delivered in the early 80’s. He didn’t give up. Instead, he persevered through getting fired and many trying years at NeXT Software to deliver the technology of his dreams. I wish more of us had that persistence. Actually I wish I had 10% of it, and I look for it in teams I fund. Good exit timing is important. But so is the drive that keeps an entrepreneur trying to solve the same problem again and again and forever feeling like he or she gave up too early.

This became clear to me a decade ago when I spent nine months cleaning up Casbah after it hit a funding wall and its founders had parted ways. I was an investor and stepped in as interim CEO and the effort extended for many months, even after I returned to my day job. This was more persistence than I wanted. But it built loyalty with investors and board members I still work with today, along with teaching me a bit about persistence.

For startup teams, here are a few things about persistence to consider:

I have been amazed when team members leave how often they don’t exercise their stock. I have even seen this happen when an exit was possible. When you leave a start up, you have to “buy” your vested stock. If you leave multiple companies you are building a portfolio, but you are doing it at a real dollar expense.

The stock you get early has a pretty low exercise price. You can choose to go to another company, but until you turn that stake to cash, you will be leaving behind a significant portion of the value of the non-vested options that’s built up while you were working at the company.

The stock you got early may have a lot of value, but without you it may be worth nothing. Startups are built on team efforts. You are more important that you think.

The people who are there are going to get more stock. You walk away from your current and future ownership when you leave. On my teams, great people, especially up-and-comers, can end up owning 3x to 6x the percentage of the company they had on day one.

What’s more, there is an enormous psychological benefit to being there all the way. I remember thinking the day we sold MerchantCircle that it would have been a lot more fun if some of those who left had stayed around. I think we would have had a better exit, and they would have, too. Buyers often structure deals to incent the teams they will work with, not those people who left.

Of course with 10-year exits persistence can be tough. But sticking with it is the way to build great companies, and it can be better for employees, too. Just look at Angie’s List and the successful IPO it launched 16 years after its founding.

Until I see another Facebook-like “sure thing,” I think I will persist.

(Ben T. Smith IV is a serial entrepreneur and investor and the co-founder of MerchantCircle and Spoke. He is available on Twitter @bentsmithfour)

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3 Comments

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  • Ben,

    Excellent article. I agree that if you are the founder (and hopefully that means you have passion/vision for the start up) you owe it to yourself (and your team) to see it through. Jumping from start up to start up creates an adrenaline junkie mentality – always seeking that next high. Kicking off a start up definitely provides that rush. If you’re a VC or Angel then it’s your job to look at new opportunities and weigh the risk/reward opportunities for each venture – and get to jump/look for new opportunities.

    Jumping from startup to start up can also create bad habits – if there is the slightest bump in the road, you get discouraged and look for the next opportunities.

    So when do you pull the rip-cord and bail? When do you come to the realization that this wasn’t the home run venture that you hoped? This is when I found it to be highly valuable to re-pitch your business model to a new group of peers. Share the original idea, and then compare it with where you are actually at today.

    If you do decide that the market has passed you by, or that the market won’t rise up to you – then you need to salvage what you can (talent, resources), keep what you learned, and leverage that gained knowledge for the next big idea.

    By the way, we met about 6 years ago in Beverly Hills. You had just launched Merchant Circle – glad to hear it was a home run.

  • I think most people would rather stay than jump ship. The fact is by being somewhere a year or two you can pretty much ascertain if the team can pull it off. People leaving is most often a no-vote of confidence on the idea / company / team – or a change in personal risk profile that merits reconsidering the decision. I find it hard to believe that people are intentionally building a portfolio of options. I do think they are looking for better ideas.

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