Things That Are Different As A More Experienced Entrepreneur

Patrick Collision, CEO and co-founder of mammothly successful Stripe, a while back put together a list of things to do from age 10 to 20 to be a successful entrepreneur.  I do wish I’d done all those things.  In a small way, a few of those age 10-20 skills I did acquire from starting a tiny software company then were what carried through to whatever success I’ve had.  But I didn’t really get started as an entrepreneur until a little later than the 10-20 age bracket ?

It got me thinking a bit about now.  At, “SaaStr Inc.” now we have a strong team, enough revenues to start taking things more seriously, and a global (if accidental) footprint.  Thought of that way, it’s the 3d start-up I’ve started, and the 5th I’ve been an executive or CEO in.  At this point, I’m an “experienced” entrepreneur.  With a house, kids, a family, and a better half that has been more successful than me.  I’ve also invested in 24+ next-generation SaaS companies, mostly successes, and had a chance to watch and learn from them as well, with a new lens.

I’ve got no great lessons or learnings on experienced vs. inexperienced entrepreneurs.  Other than be careful about age-ism.  The skills I’ve learned are 90%+ transferrable to this generation of SaaS companies.  Maybe more.  And age-ism is going to cut out some of the very, very best talent in the market.  It’s hard enough to find great people as it is.  My general rule for start-ups is “young at heart”.  Hire folks of any age that are young at heart, with a joy of discovery and learning, and special things happen.  And paying a little more for a lot more experience can be one of the top investments you’ll ever make.

Still, an overall deep-dive on lessons learned the second and third time around:

Not Easier:

• Recruiting – Not Easier.  You might think after (goodness) the best part of 20 years of working in tech, 18 as an executive or CEO, and 13 as a founder … I’d be pretty good at recruiting at this point.  I’m not.  Perhaps, I am worse.  In the early days, especially as a first-time founder, I thought I could recruit anyone and everyone.  That I had such a superpower, they would all join me.  I’d fly anywhere, convince anyone.  And it sort of worked.  Not always, but definitely sometimes.  Now, I’m much more focused on making sure hires have a great career path and growth potential ahead of them.  And flying somewhere crazy for an interview, or doing 30 interviews a week, is … harder.
• Sales — Not Easier.  As odd as this may sound, I personally am not any better at sales than the first time around, and maybe worse.  In my first start-up, with my naivete, I closed $6m in bookings in our first 6 months.  The second time, I routinely closed big customers that looking back, we didn’t deserve.  Now, I’m more careful with the odds and my time.  I know how sales works much, much better.  But I’m not as good at getting on jets myself.  I’m personally a worse salesperson. I need more help to scale sales, to build the relationships, and to do the cookie-cutter parts.  I’m much better at setting the stage for sales now, providing the platform, adding value.  And I worry much, much more about providing true value for customers, perhaps to a fault.  But I no longer believe I can close the impossible customer.  I let those go.  And … I used to close the impossible ones.  So maybe that part is a loss.
• Building Software — Not Easier.  I’d like to think in this low code + API age building software is somehow easier.  It isn’t.  It’s still a people business, and one with power laws, where the very best engineers just do magic.  The language, the platform, the stack don’t really matter.   And in 2018, the bar for great SaaS and enterprise software is higher than ever.  So even though we built some custom SaaStr software in the early days with the help of some great engineers, I’ve backed away from that, and am focused on using off-the-shelf tools.  And it turns out, you can probably get to $25m using off-the-shelf tools these days.  Not elegantly, or optimally.  But it’s not impossible.
• Getting on Jets.  It does get harder.   This is a disadvantage.  I used to fly to Pittsburgh, for example, for a day trip to recruit an advisor.  I’d go to Buffalo for a quick meeting.   Minneapolis in the -20 degree dead of winter to just “drop by” a top prospect that wouldn’t schedule a meeting.  Ditto Chicago with its brutal winds.  Or Japan.  Now, that’s all a lot less appealing.  Honestly, I just don’t do it that often anymore.  Just a few times a year.

What Is Easier:

• Seeing the Future is Easier.  We had 1,500+ register for the first SaaStr Europa the other day, and over 1,250 on site.  I told the team we’d have about 1,200.  They thought I was crazy.  But I knew.  After all, we had 1,000+ for the first SaaStr Annual in SF in 2015, and had to cap attendance.  Getting 1,200+ to the first SaaStr Europa was sort of the same.  Different, but the same.  So I also know we’ll have about 2,500 next year at the 2019 Europa.  CEOs will bring their teams, word-of-mouth will spread.  And we’ll have 2,500.  That makes planning much easier when you already know.
• Investing in the Future is Easier.  Every cent we’ve made from SaaStr, I’ve re-invested.  My salary is still $0.  That’s easier now.  It’s not just because we have some savings, although that’s part of it.  It’s because I much better understand the power of going long.  I know what SaaStr will look like in 2019, 2021 and 2022 at least, and maybe even 2024.  I want to invest in that future.  It won’t be easy operationally to pull it off, but I like what I see when I squint into the future.
• Going Long is Easier.   A similar point to the prior one, but after 5+ years of building SaaStr, I can see the next 5 years can clearly be even better.  The community, the events, the content, everything.  It can all just get better.  And I’m in on that future.  As a first-time … and maybe younger … entrepreneur this was harder.  Everything seemed so fragile.  I could see the future, but it was more like many variants of the future.  The good outcomes, the middling ones, and the rougher ones.  I knew where the market was going, but I didn’t know the playbook as much.  It seemed risky to go long operationally.  It doesn’t now.
• The Playbook Works.  And Running it is Much, Much Easier.  I know who to hire, when, and how.  I know the gaps.  Even if recruiting isn’t easier, at least I know exactly who we need.  Things change, markets change, and you have to update the playbook.  But most of it works.  I know how SaaStr can be a $100m business now.  It may not happen.  But I know how.  In my prior start-ups, I knew what it would take, the model, the growth.  But I hadn’t internalized the playbook.  Now I have.
• I Care About the Team Even More.  I always cared a lot about the team.  I prided myself in my first two start-ups about having zero voluntary attrition.  But ultimately, I felt a lot of things were out of my hands.  What the investors would do, what an acquirer would do, who a new VP would keep or not keep, etc.  Now it’s all in my hands (bootstrapping helps, too, but going long is the key).  So that puts a bigger obligation on me to deliver for the team, but it also gives you more freedom to do what you know is right.
• You Don’t Sweat the Small Things.  This may be trite, but it’s true.  It’s easier to let the small things go.

What is DIfferent:

• Short Term(ers) are Of Little Interest.  When I was a first-time CEO, I thought about time differently.  I was just trying to hire anyone wicked smart to help.  But now I see that any key employee that doesn’t stay at least 2 years is sort of a wasted investment.  Most employees only really get great once they’ve been through a cycle or two.  That’s often Year 2 when they get great, and then Year 3 when they can become a leader / great manager.  If they are going in 10 months, that’s no longer of any interest to me.  I’d rather not make the hire.   I quickly try to figure out why SaaStr is a good fit for a potential hire for 2-3 years at least.  I didn’t used to worry so much about this.
• Brand, Brand, Brand.  If You Have It — Protect It.   You have to have been doing it a while to understand the power of brand.  Trusted, proven brands are highly defensible.  They are how middle and late adopters make decisions.  Even with very limited marketing and a tiny list, for example, we’ll have 10,000+ come to the 2019 SaaStr Annual.  So I worry much more about delivering against that brand, and not harming it.  This is why we never sell speaking slots, for example, or the list.  Why we reject speaking sessions even from Decacorns that are commercials.  Why we don’t anything that doesn’t add value to our community, period.  SaaStr has to put community first, second and third.  Protect that brand … and it builds on itself.  Brands become global, and they last decades if you do it right.
• It’s Harder to Do Anything Else.  After I sold my first start-up, I took 10 months off and was pretty happy.  Hooray!  I’d been a reasonably successful founder with a decent exit!!  But after I sold the second one, I was pretty miserable.  I couldn’t do anything else.  I needed to build, to contribute, to add value, to help take something from nothing to something real to something special.  Anything else was just not enough.  Not at all.
• Relationships and The Journey Are All We Have.  You learn this the first time around for sure, but you really get it later.  I don’t really care what I do, personally.  I’ve built 3 very different companies.  The exact companies I started sort of chose me, in some ways.  I’ve built products that saved lives, and ones that created categories.  That’s not really what I think about so much.  It’s the team and the journey you’ll remember.  The innovative products we build today may well not be around once we’re 100.  But hopefully, some of the team will still be there.  I hope when I’m 100, I’ll still be able to get together with some of my co-founders, executives, and top teammates.   The third time around, it’s not worth it without a team you truly want to go on a journey with.

What’s the Same:

• Imposter Syndrome.  Still have it.  Almost every day.  I’m just a little more at peace with it.  I try not to hang out with people, or at events, that accentuate it ?  I try to spend more time with folks that care about what I care about, with similar values.  I still try to hang out with CEOs and executives that are better than me.  That’s what pushes you to the next level.  But I try to avoid folks that have no idea what SaaStr is, and more importantly, don’t care and don’t want to learn.

In the end, I think third-timers do have some cons.  The crazy stuff is harder now.  The travel is harder.  And I get tired at night now.  I used to make explainer videos at 10pm.  Now I’m trying to get shut-eye around then.

But it’s easier to go long, and go big.  Maybe at a minimum, it’s a wash.  It’s certainly not a negative to be more experienced.

So maybe add some more folks with solid experience to your team.  You probably don’t have enough of them.  We may not be as crazy.  But we do know how to get you there.

(note: an updated SaaStr Classic post)