Dear SaaStr: What’s Your Best Advice for Struggling Entrepreneurs?

Having struggled a lot myself in the early days several times … just a few thoughts to summarize my learnings:

1.  Get help & upgrade the team.  This is the #1 thing you can do to move the needle.   Don’t be ashamed to ask for help.  Especially if you are struggling.  And if you can, just go hire 1 great leader, one great VP or even 1 incredible individual contributor.  It really does make a difference, adding one more truly great one to the team.  It always does.  In my toughest times, it was always adding one great leader that turned things around in the end.  Just one great one.

2. You may be doing better than you think.  This is a mistake many entrepreneurs make once they have the tiniest bit of product-market fit.  I know you aren’t doing as well as Figma or OpenAI.  But it’s possible you are doing better than you think.   If you got 10, 50, 100 businessess to actually buy Yet Another SaaS Product — that is something.  Real.

3.  Get a (better) mentor if you can.  This doesn’t have to be Marc Benioff.  What it does need to be is someone at least 18-24 months further down the road than you.  They’ll help you see what’s working and what isn’t.  More on that here: SaaStr | I Don’t Know about CEO Coaches.  But We All Could Use CEO Trainers.

4.  Buffer for even more time.  Great founders almost always find a way to pull it out in my experience.  Running out of time becomes the enemy.  So find an extra 8-12 months of time.  Of runway.  Of capital.  Of committment.  Of everything.

5.  The 1.0 isn’t supposed to be great.  Final advice if you are a perfectionist.  It’s supposed to take iterations.  The first version doesn’t always work, nor sometimes, the third.  It can take longer than you’d hoped to ever really understand what your customers really want.  And then even longer than that to convince them to somehow buy from you.  Don’t quit.  As Auren Hoffman wrote in another post, of all his seed investments, the only ones that have truly failed are where the founders quit.  Same with me.

6.  Spend time with founders doing a smidge better than you.  Spending time with founders doing radically better than you doesn’t always inspire in tougher times.  Sometimes, they can burn you out. But if you’re growing just 20% a year?  Hang out with a CEO or two at 40% a year growth.  They may inspire you to find a way to grow another 20%.  Events like SaaStr Europa and Annual are great for this.

7.  Just go talk to most of your customers.  Just listen.  In person.  They will almost always show you the path to doing just a smidge better at least.  You know your product.  But they know their pain even better than you do.  And what they’d pay for, to get even more of it solved.

I’m seeing more and more CEOs quit these days.  CEOs of startups with millions in revenue.  That may feel better for a week, a month, a quarter.  But rarely after that. Building something customers actually want and will pay for is special.  Even if some patches don’t feel like it.

>> Don’t quit. <<

A related post here:

Never Quit If

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