If You Go Small, You’ll Never Have a Legacy

Small can be beautiful in start-ups.  Take no venture capital, build an eight-figure business, put the profits all in your backpocket.  You can end up having a villa in Italy full of Pagondis, like the Basecamp guys.  Boom.


The thing is, if you don’t have a legacy, how much will it mean to you in the end?

I started to think about this a lot recently when Adobe integrated EchoSign into Acrobat.  The first integration was Reader, which has a much larger footprint (1 billion+ devices), but because it’s free, isn’t really a customer commit per se.  But integration into the $800m-ish Acrobat suite means a 10+ year customer commitment.  That means, almost no matter what the future holds, EchoSign is guaranteed a longer future ahead of it than it’s already had. Millions and millions of users for at least a decade to come.  10 years is almost forever in internet time.  It’s as permanent now as any web service can be.

This permanence is something you really have to Go Big to get.

The first start-up I worked at was BabyCenter.com in the Web 1.0 days.  While BabyCenter has gone through a number of changes over the years, and now is part of Johnson & Johnson, it’s still in the Top 350 websites on the web — after 15 years.  15 years in the Top Few Hundred web sites.  And luckily, now that I’m older, and most of my contacts and peers and friends have kids — they’ve all used it as well.  So that’s a nice little legacy to have been a part of.

The first start-up I co-founded actually, from a Changing the World perspective, did more than anything else I’ve ever done.  At NanoGram Devices, our technology has gone on to save hundreds if not thousands of lives.  We also delivered a 600% return in 13 months and made good money.  And the founders have gone on to found 3 more industry-leading start-ups.  But, the brand, the product, our labs, and much of what we “did” is gone, rolled into our acquirer.  Despite Changing A Little of the World, there is no legacy.

I have no bias on going big or small.  But if you want a legacy, you have to Go Big.  Though maybe that’s best to think about in your second start-up.  Perhaps it’s a luxury.

There are 10 comments

  1. Bob Warfield

    Don’t worry too much about the Basecamp guys, Jason. Ruby on Rails makes a fine legacy for them.

    If you want a legacy, it’s often hard to come by. It has little to do with going big or small and everything to do with whether what you do matters. Go with your heart.



  2. Brendon Cassidy

    If you do a startup, legacy is measured by one thing and one thing only: did you exit? You either go public or get acquired. Either of those happen, it’s a variable degree of success. If your startups don’t exit, then you have no legacy and it’s time to go back to taking orders at Oracle.

    Pretty simple.

  3. jasonlkn

    I agree, and maybe that’s all it is — and I used to think that’s all it was.

    But maybe it’s because I am older now, and have time to actually think about these things, I think there’s more than that. EchoSign had a great exit with is a necessary part of legacy, but it’s now more than that — as one example. Having it part of Acrobat for 10+ years means it has a permanence beyond its other successes. I think that’s pretty neat.

    There are other great exits, where the product fades away in 12 months. I don’t see much legacy in Slide, or Aardvark, though the returns looked just fine and Google is a great acquirer.

    Again though, seeing legacy as anything more than a successful exit to a tech leader or successful IPO may be a luxury at best. I never thought much about it before.

  4. Aaron Ross

    Seniors looking back on long lives don’t say “I wish I’d created a bigger business” or “worked harder”. They say they wish they’d spent more time with their loved ones (or even loving), or wished they’d taken more risks like even starting their own business.

    After a few years or decades, you won’t care at all if you went Small or Big in business compared to whether you went Small or Big in your relationships to other people….such as spending more time with your kids while they’re kids… unfortunately too rare and hard to do for many working parents, especially entrepreneurs Going Big.

  5. jasonlkn

    True enough. The problem is, ALL start-ups take 100% of your time. All your thoughts, all the time.

    So if you can, you might as well Go Big and Have a Legacy. Because it’s actually just about the same amount of work (not risk, but same amount of work) IMHO.

  6. Bill Moore

    You think anyone will know who Bill Gates is in 100 years? A small group of historians, that’s it. What matters is how happy you are now.

    The basecamp guys nailed it.

  7. Nick Mehta


    I love this post because it’s thought provoking. I agree with it and disagree with it at the same time. As F. Scott Fitzgerald said: “The test of a first rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.”

    In that spirit, I totally agree with this in terms of seeing what makes entrepreneurs and leaders feel good years later and hearing what they’re proud of. It’s never the money or the exit. It’s always the legacy. This is what explains why guys like A16Z, Sequoia, Bezos, Ellison, etc. keep going for it. They have more money than generations will ever need. They are playing for legacy.

    At the same time, I always try to remember that legacy is an illusion: http://en.wikipedia.org/wiki/Ozymandias


  8. The Second-Timers: Mark Organ, CEO/Founder of Influitive and Eloqua: “10 Hard-Won Lessons” - Enterprise Irregulars

    […]     Swinging for the fences – While I did have big dreams at Eloqua, I was mostly concerned with surviving another quarter, another year.  This time, we have higher ambitions, we want to win it all.  And that means extraordinarily high rates of growth, with minimal decay rate on that growth. High growth in every time frame – this month, next quarter, next year, 3-5 years from now. Think about how Salesforce or LinkedIn is practically a different company every year, in order to keep their growth rate as high as possible. It means that the seeds of the next growth idea must be planted ahead of time. It means that the barriers against future competition need to be erected early. And it means that we and our investors will get a strong return from equity financing. Jason discusses going big on round 2 in a great post here. […]

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