Just Binge-Listened to 95 SaaStr Podcasts, Here's What I Learned

February 6, 2017 by Ken Kaczmarek

Who needs a #drinkwithharry?

Over the past few weeks, I tasked myself with listening to all ~32 hours of the SaaStr podcast, in preparation for the SaaStr Annual conference. Each show is an incredibly dense, 20-minute nugget on the business of SaaS. IMHO, it is totally and completely worthwhile to meander through twice-weekly.

However. Powering through them all in one go was the equivalent of a Brain Blaster—more like binge-watching Planet Earth than Portlandia. Do as I say, kids, not as I do.

So, what did I learn? Well, a ton. Let’s try to unpack the highlights with the Data, the Recommended Resources, the Words of Wisdom and, finally, the Personal Lessons.

To the Data!

As part of this journey, I put together a file that combines data from the RSS feed along with my own note-taking on each episode (typos and dirty data notwithstanding).

The CSV is available on GitHub. We also knocked out a super simple search app here (shameless plug: we use a Flex.io pipe to add this dynamic content to this static post, here’s the how-to guide):

Fun facts:

  • 54% of episodes featured a CEO and/or Founder
  • 21% of episodes featured a VC or other Investor
  • The remaining episodes (with a few exceptions) were with VP of sales, marketing or customer success
  • Of the non-VC interviewees, there was a diversity of SaaS products on display. HR and Marketing companies were most prominent (~30%), but others ranged from security-guards-on-demand to shipping APIs to a Slack bot. It’s a big world out there.
  • There were only two repeat guests (Jason Lemkin and John Barrows)
  • The “60-second SaaStr” was nicknamed “the Churn” for a few early episodes. The “Good, that’s perfect, I think we’re warmed up” audio snippet appeared 43 episodes in. Were these the experiments and casualties of lean podcast methodology? We’ll never know.

This is probably a good time to note that Harry Stebbings, the wunderkind interviewer, is a natural. In addition to tight, relevant questions, the brilliance of the show really comes down to the editing. 20 minutes is a perfect length and a huge differentiator compared to other tech and startup podcasts.

One question Harry often asks (~55% of all interviews) is simply: “What are your favorite SaaS resources?” Interviewees answer with various blogs, books, podcasts, among others. I compiled each resource and grouped them by number of mentions. To make things a little easier to read, I also highlighted the books in blue:

Resources SaaStr Final

There is clearly a preference for SaaStr on these Saastr podcasts (weird!), but you clearly don’t want to miss out on Tomasz Tunguz or David Skok either. When you go to google “How to Castrate a Bull” make sure you add “business book” to your search criteria.

Words of Wisdom

As for actual content, where to begin? It’s an embarrassment of riches. So as not to write a novel, let me give you a taste by simply quoting from a handful of interviews (with gentle editing for clarity):

Nick Mehta, Gainsight, Episode #24 on What Companies are Getting Wrong with Customer Success

“#1 they think it is just about churn reduction… just the beginning of the story… it’s about upsell, expansion and most importantly about advocacy and getting your customers to be your best sales people…#2 they hire the wrong leader… maybe passionate about the customer and product, but not operationally focused…#3 they put it under another exec… part time responsibility of marketing or sales… #4 they make it all about people and heroics v. process… #5 they think about it as just the CSM team’s responsibility, when in reality that customer success team is the quarterback… but you need the whole company to rally around it.”

Aaron Ross, Author, Episode 46 on the Most Common Reason Companies Struggle to Grow

“Because they haven’t nailed a niche… you can have a big vision, but it means being very focused—baby steps—around the type of customer segments… who today you can find, talk to and who need you enough to buy from you… so you can double-down and grow fast.

An old story, company has a product, anyone in the world can use it and get value from it, but no one is buying it. Where are you a need to have vs. where you are a nice to have? It’s hard to have the internal discipline in the early days to say these customers can all use us, but they don’t need it so much that they’re going to buy… got to focus on these 1-2 very specific areas… maybe not sexy… but enough of a pain there that they’re going to need us and go through all the huge time and energy and effort—the more-than-you-expect-process—to evaluate us, buy us and deploy us.”

Russell Glass, LinkedIn, Episode #14 on Marketing within the Customer Lifecycle

“At each stage… [customers] have certain information needs… and if you can, as a marketer, help them with those information needs at the right part of the journey of that decision, that is when you are relevant… that is when you are able to transcend being marketing material and move into the information universe.”

Seth Besmertnik, Conductor, Episode #79 on Weaponizing Marketing:

“Your marketing can be a weapon and core competency and differentiator… [for a crowded market] what ends up discerning the difference is the marketing… are people finding you?… do they know you exist? There are a lot of great software companies that are dead on the side of the road because no one ever found their business, no one found their product and they weren’t good at sales and marketing. So having a great product is the start, but it’s not how you get across the finish line.”

Mathilde Collin, Frontapp, Episode #10 on Content Marketing Strategy

“We have a process, first try to release at least two posts per month… and then always try to write 1/3 on market we’re in… 1/3 on our journey… and 1/3 about specific use case for customers”

Peter Reinhardt, Segment, Episode #80 on Turning Up Product Market Fit to Eleven

“[Early on] we managed to convince ourselves that pretty meager levels of customer excitement meant product market fit, which I think is an easy thing to do… I think customers have more dynamic range in their response to a product than most people realize… “oh that seems helpful”… 7 or 8 out of 10… but when you really hit a pain point, the customer’s dynamic range goes up to 11… and their response is totally different… like holy shit, can I get access to it today? I need to call this other person on my team who has been talking about this forever, how ‘bout I introduce you? and you’re like “woah, woah” it doesn’t even exist yet, slow down… I think the customer’s dynamic range is much broader than we realized and so we never actually hit that 11 and just convinced ourselves that 7 out of 10 was product-market fit.”

Ryan Smith, Qualtrics, Episode #83 on Necessity of Managing Runway

“Rome wasn’t built in a day… it’s going to take time, if you can keep your options from a funding or partner standpoint to actually give you a long enough runway, entrepreneurs will figure it out. The problem is when they put a stopwatch on their back… every bet that we’ve made has taken a little longer than we anticipated… you don’t want to limit yourself to one point in time… you gotta play the long game.”

Leo Widrich, Buffer, Episode #89 on an Embarrassing MVP

“The quote… that you should be embarrassed by your first version gets misinterpreted a lot… you shouldn’t be embarrassed because it completely breaks or is unusable… that’s the wrong type of embarrassment… the type that is good is the embarrassment of richness… like, kinda embarrassed because it’s only this one feature and you wish you had done three more… it is complete unto itself… not the base layer of the cake, but, instead, a cupcake.”

Personal Lessons Learned

If there is one thing I’ve personally learned throughout this process, it’s that the 2x speed on a podcast app is probably the greatest invention of all time.

But, as far as SaaS goes, I think what you receive through drowning in all this content is a solid understanding of the conventional wisdom of running a SaaS business, from early days to scale. Things like:

  • Hire athletes in the beginning, specialize later.
  • Initial product market fit is when you have 10 unaffiliated paying customers
  • Sales and Customer Success need to be working in tandem, given the necessity of retention in SaaS
  • Don’t spend money on sales until you have a repeatable process
  • Focus early on a single persona
  • Get people to pay you early
  • More mojitos, faster

Another cool thing about this binge-mission, should one accept it, is that you’ll certainly find a few tidbits that speak directly to your situation. For instance, I almost fell out of my chair when Harry Glaser of Periscope Data (Episode #30) was asked about greenfield opportunities in SaaS and then went on to lay out the problem that our startup, Flex.io, is trying to tackle:

“I think one thing we see that maybe other folks don’t see there’s a lot of back end data munging and processing and kinda unsexy data things going on that are really being done with a collection of hacky python scripts right now… copying data from place to place, transforming data, storing data, all that stuff is being done by people writing scripts on the side… so I think there is a big opportunity there…”

Let’s hope so, Harry!

Well, I hope this proved to be a useful summary for you, dear reader. Lemme know what you think in the comments or hit me up @flexiodata or @wanderslth.

May your SaaS companies flourish and may your mojito glasses never be empty! Hope to see you at SaaStr Annual.