The Lawyer Who Became the King of SaaS

Jason Lemkin Lawyer

From lawyer to tech start-up guru, and the undeniable thought leader for the SaaS movement in Silicon Valley, Jason Lemkin continues to build a following of founders, CEO’s and sales execs through his blog SaaStr. With the support of Storm Ventures, Jason recently wrapped up his first major event, SaaStr Annual, where 2,000 founders and execs met in San Francisco to discuss how to build and scale a SaaS business. We were fortunate to interview Jason and get his perspective on how law school shaped his early career and how young attorneys looking to transition into tech should approach the jump. 

Jason M. Lemkin graduated from Berkeley School of Law before entering the world of Silicon Valley tech start-ups. Today Jason is a Managing Director at Storm Ventures, an $800m AUM venture capital fund.  Storm has been the first or very early investor in many leading enterprise/SaaS start-ups, including his own EchoSign (acquired by Adobe), Marketo, MobileIron, Appcelerator, Sandforce, Metacloud, Guidespark, Pipedrive, Algolia search-as-a-service, TalkDesk, Parklet, Metacloud, RainforestQA, and more.

Jason Lemkin

Jason Lemkin graduated from Berkeley School of Law before entering the world of Silicon Valley tech start-ups.

Jason has co-founded two successful start-ups selling to the enterprise.  Most recently, he served as CEO and co-founder of EchoSign, the web’s most popular electronic signature service, from inception through its acquisition by Adobe Systems Inc.

He then served as Vice President, Web Services at Adobe, where he oversaw the growth of EchoSign and Adobe Document Services to $50,000,000 in ARR in 2012 and $100,000,000+ ARR in 2013.

Prior to EchoSign and Adobe, he co-founded one of the only successes in nanotechnology, NanoGram Devices, which was acquired for $50m just 13 months after founding.  The technology, built into implantable power cells, has gone on to help extend the lives of thousands.

Jason has no known hobbies.

LI: Did you go to law school intending to become an entrepreneur?

JL: No.  It was merely that by being at law school in Silicon Valley during the rise of the Internet, my earlier entrepreneurial leanings were rekindled.  I then tried to leverage law school as much as I could there, joining a 100% start-up focused law firm, Venture Law Group, upon graduation.  I also took as many classes at the business school while I was in law school to expand my knowledge base.

LI: You’ve had a couple of big wins in Silicon Valley, how did your legal background contribute to your success?

JL: My “legal background” in the sense of being a corporate attorney for 23 months did not help.  I wasn’t a great lawyer.  I was incredibly passionate about my clients, but I wasn’t detail-oriented enough to be a great lawyer.

But, what I learned from the sidelines, and who I met as a lawyer, helped inordinately.

My first post-law firm job was joining one of my clients, and that never would have happened in that sequence otherwise.  My bosses there remained my mentors, investors, and friends to this date.  And they forced me to learn to be a manager.  You don’t learn to be a manager at a law firm.  Lawyers are terrible managers.

And from watching the boards of 20+ start-ups as an attorney, that gave me the confidence to become first a start-up executive, and then a founder.  I had seen it done 20+ times, sometimes well, sometimes in failure.  But I knew roughly the playbook, at least at 20,000 feet.  Turns out I had no idea how to really do it, but at least I knew what the cadence of a successful VP and a successful CEO looked like.  Because I’d seen them up close in 100+ board meetings, over 2 years.

Finally, law school itself was helpful, but in a nonobvious way.  What law school taught me was how to work truly, insanely hard.  After my first semester, my grades were mediocre.  I was determined then to get in the top 10% of my class.  My second semester, I had almost perfect grades, and ended up one slot shy of Top 5%.  This had nothing to do with intelligence, or passion for the law.  I was not in the top 10% smartest of my class.  Not by far. But I worked incredibly hard.  Harder than almost anyone else.  Turned out for me, at least, it worked.

And it turns out to be a founder CEO, and to make it … you’re going to have to do that as well.  Work 10x harder than any VP you’ll ever hire.  It’s incredibly hard.  Every moment, of every day, of every night, you’ll be obsessing with how to make your start-up a success.  Every second.  Without those law school exams, I wouldn’t have been tough enough for either of my start-ups.

LI: We receive lots of emails from young attorneys who are interested in transitioning into tech. What suggestions do you have for them? Is there a certain type of tech company or a job title/function (e.g. business development) that is a good starting point?

JL: In some ways, these transitions are harder today.  Now that the internet is so much more mature, everyone wants a director of business development that used to be at Salesforce, Twitter, Facebook, etc.  Not a law firm.

My real suggestion if you want to leave the practice of law is first, look for your break.  It’s probably going to come from someone you’ve worked with.  Not a job posting.  That’s where someone will take a risk, with someone they know and trust, even if the resume isn’t perfect or mature yet.   And second, know yourself.  You may take a large salary hit.  Doing that earlier can be much easier than later.

unnamed-2And if you’re on the fence — let me challenge you.  Most lawyers are way too conservative to make it in start-ups.  CEOs don’t want someone that just identifies risk.  Or says no.  Or even just says yes.  They want problem solvers that get things done.  That solve real problems in the enterprise.  Period.  Is that you?  It’s not 90% of lawyers.  Most just give you an analysis.

LI: As a co-founder of EchoSign, an electronic signature software, what’s your take on LegalTech like RocketLawyer, Shake and CaseText?

JL: As a VC now, I’m not that interested in legal as a vertical.  I’m not interested in selling to lawyers, per se.  It’s just not large enough to produce a unicorn.

However, there are two areas I’m very interested in.  The first is legal exposure.  That’s a top issue for every enterprise.  So I’m investing now in a next-generation eDiscovery company that brings the power of eDiscovery to any company, governments, and smaller matters.  Another is the collective purchasing power of individuals and companies.  This is what RocketLawyer is really tapping into.

But selling some tool to help lawyers practice better?  Usually just way too small a market.

LI: Your SaaStr blog receives over 750k page views per month and 6 million+ views on Quora. What advice do you have for bloggers out there who are trying to build a following?

JL: My “success”, such as it is, was an accident.  I told my story — across 1,300 total posts and answers.  What I screwed up, and learned, on the way to a pretty solid exit.  But an exit I probably wouldn’t do again … I wouldn’t have sold in ‘15.

I don’t think any of it is profound.  I didn’t invent a browser, as Mark Suster kidded me.  But what it is — is authentic.  It’s a real story going from $0 to $100m in revenues, with no drama, no baloney.

That hit a chord.

So what I’ve learned is what we all know — be authentic.  And focus on something you personally know well.

And keep at it.  It took 12 months for me to build a real audience at SaaStr.  It took over 2 years until it was big enough to have a founder conference in February with over 2,000 founders in attendance.

Next year we’ll have 5,000-10,000 folks at the 2016 Annual and millions of views per month.  But it will have taken 3 years.  And 2000+ posts and answers.

Follow Jason on Twitter: @jasonlk

About Preston Clark

Preston Clark has been writing about legal tech since 2010. He's currently the CRO for a leading legal tech SaaS company in the San Francisco Bay Area. Preston was formerly in-house counsel for the University of Miami and a Peace Corps Volunteer in Central America. In his free time, Preston enjoys building world-class sales teams, reading about SaaS, playing pick-up basketball and planning adventures with his son.