Book: All Over The Place

I’ve written this post in the style Geraldine used in her book. As you read this, assume that I’ve failed miserably at it and Geraldine is 1000x funnier and more clever than I am.

I had a weekend of books. Amy’s cold drifted over into my part of the world so I slept a lot, ran a little to try to clear out the goo in my head, and read until I feel asleep again. And I ate nachos, several times, which I never do at home.

Last week I ordered 51 hardcover copies of Geraldine DeRuiter‘s new book, All Over the Place: Adventures in Travel, True Love, and Petty Theft, from Amazon. I did it to celebrate that my 51st year on this planet coincided with the publication of Geraldine’s first book. I brought two of the books home – one for me, and one for Amy. I think I’ll make a chair out of the other 49.

Geraldine writes a popular travel blog called The Everywhereist. Amy has characterized it as “pee in your pants funny” which I’ve never actually experienced, but I think I understand. Geraldine’s book doesn’t disappoint, as I wandered to the bathroom several times while consuming the 274 pages on Saturday. I laughed out loud a lot, but I also drank two bottles of Pellegrino in an attempt to stay hydrated.

All Over the Place is a memoir masquerading as a travel book. Geraldine starts off strong with a disclaimer which points you at what the journey of this book will actually be.

“So, if there is any advice I could dispense, it would be this: it’s absolutely incredible, the things you can learn from not having a clue about where you’re going – lessons that emerge after making a wrong turn, or saying the wrong thing, or even after accidentally doing something right. And in my case, this was all undertaken not in the company of a new love, but one that has enough miles on it to circle the earth three, maybe four times, is now sufficiently jet lagged, and lost its pants somewhere over Greenland.” 

If you know Geraldine’s husband Rand Fishkin, you may recognize him as the not a new love. I learned a lot about Geraldine and Rand in this book, including their experience with poop and toilets, but is gender reversed from the experiences Amy and I have had (hint: Rand and Amy are the heroes of those particular stories.)

The chapter titles give you a feel for what you are in for:

  • Marry Someone Who Will Hel You Deal with Your Shit (see above paragraph)
  • Home Is Where Your MRI Is
  • The Contents of My Mother’s Carry-On Look Like Evidence from a Prison Riot
  • Life Lessons from a Three-Hundred-Year-Old Dead Guy and His Boring Clock
  • Gelato Is an Excellent Substance in Which to Drown Your Sorrows

I think y’all know I’m a big fan of chocolate gelato. Which is what I went out and got after I had an extremely uncomfortable phone call with Geraldine after realizing that she’d found out that FG Press wasn’t going to publish her book by noticing that we’d taken her off the FG Press website as a future author. Of course, this was totally my fault, as I’d told the FG Press gang a month or so earlier that I’d call Geraldine to tell her we were shutting FG Press down and, as a result, wouldn’t be publishing her, or any other, books. I apologized 49 times, went out and found a chair to sit in, and had a chocolate gelato. I think she eventually accepted my apology, kept working on her book, and found a serious publisher (PublicAffairs/Hachette) who did an awesome job with All Over the Place.

I’m extremely proud Geraldine. Her first book is extremely true to her writing, her soul, and her soulmate. I learned a lot while reading it, and not just about Geraldine and Rand, but about life.

The Journey From $1m MRR to $2m MRR

There’s a long-standing cliche concerning SaaS companies that once you get to $10m in ARR you are unkillable. As Jason Lemkin says in his post from early 2013:

Inevitability in SaaS comes around $10m in ARR, plus or minus. Once you hit this point, you have a brand, you have a fully baked team, you have a robust product, and you have a self-generating stream of new leads and new business. Will you get from $10m ARR to $100M ARR? I don’t know. Is an IPO in your future? Not sure. But once you hit $10m in ARR or so, you cannot be killed by anything. That’s the power of compounding SaaS revenue. And actually, as we’ll get to, $10m in ARR — this is when it really gets fun.

I’ve struggled with this concept and how to translate it into action in my world. While the phrase “you cannot be killed by anything” is evocative, your actual value can be killed, as there are many problems getting from this stage (whatever we are going to call it) to the next level.

I don’t like to think in ARR when I’m working with SaaS companies. I’ve always found MRR easier to process, especially when thinking about derivative measures, like growth rate and churn, that are so important to pay attention to on a monthly basis. And, instead of ARR thresholds ($10m ARR, $25m ARR, $50m ARR, $100m ARR), I like to use MRR thresholds, which I talked about extensively in a post from 2015 titled The Illusion of Product/Market Fit for SaaS Companies. The MRR thresholds I focus on are $1, $10k, $100k, $500k, and $1m. And $1m MRR is the particular moment that is analogous to the $10m ARR inevitability.

If you can blast through the $500k MRR mark and march to $1m MRR, you’ve found product/market fit. You are now at the magical point some people call “Initial Scale.” Cool – you’ve got a business.

If you believe the cliche, you are now unkillable. I’d suggest that instead, you are now in an entirely different zone as a company, where you will be evaluated on a different set of characteristics and will face different struggles. If you want a hint, read Fred Wilson’s recent post titled Team and Strategy.

If you are a CEO, the real work of scaling a company begins about now. The question you’ll be facing will have a lot less to do with product (and the product strategy), and a lot more to do with – well – strategy!

You can start exploring questions like: Are you the market leader? Who are your competitors? What are you doing to build a moat around your business? If this sounds like Competitive Strategy, instead of Strategy, it is, but it’s a critical starting point. If you don’t want to read Porter’s classic book (or read it again if you read it a long time ago), try a Wikipedia shortcut on Competitive Advantage.

You can shift to more specific questions around a category like sales such as: Are you making progress on lowering churn? Have you moved from monthly to annual deals? Are you trying to get three-year deals done? What is the composition and health of your channel?

These are all things that you likely ignored, or didn’t even think of when you were in the $100k to $500k MRR zone. Well – maybe you thought about churn, especially if it spiked up to a point as to undermine your growth rate and cause another cliche – the leaky bucket – to appear in all of your board discussions. But did you shift from monthly to annual deals so that you could lower your long-term capital needs significantly? If you did – great job!

We have many companies in our portfolio in the $1m MRR to $2m MRR zone. It’s fun, but challenging in a different way than the up to $1m MRR zone is. And, once you blast through $2m MRR, all the things you focus on as a CEO change again.

Venture Deals Online Course – 2017

The Venture Deals Online Course for this spring starts this Sunday May 14, 2017 and runs through July 3, 2017.  The Kauffman Fellows Academy and Techstars are co-hosting the course. It’s free – all you need to do is sign up.

This is the fifth time we are running the course. So far more than 5,000 people around the globe have done it and we’ve gotten to meet and collaborate with entrepreneurs from six continents.

While our book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist is the basis for the course, we have extensive exercises, additional content, and a highly engaged community to answer questions. Jason and I make regular visits, both in the online discussion sections as well as periodic AMAs. In addition, the team from Techstars is also engaging throughout the program.

If you are interested in entrepreneurship and how startup deals work, here’s a great chance to go deep on this with me, Jason, Kauffman Fellows, and Techstars.

Helping To End The Stigma Around Mental Health By Talking About It

I’m super lucky. I get to work with many incredibly brave and insightful people. One of them is Chris Heivly who is now working at Techstars with me and a few others on a new set of products around the concept of startup communities.

May is mental health month. Jenny Lawton, Techstars COO, led off Techstars commitment to engaging with the post Let’s End the Stigma Around Mental Health. Her call to action, before she goes on to talk about her experience with mental health issues, follows:

“May is Mental Health Awareness month and Techstars is driving to end the stigma that surrounds mental health. Let’s open up the conversation around it and what it means to our community and industry.” 

Today, Chris went public with his story in the post That Time I Could Not Break My Depression. If you’ve never met Chris, he’s a gregarious, energetic, fully engaged entrepreneur who has had multiple successes. But, he has struggled with depression, as he says in the lead off of his story.

“None of that prior success prepared me for a moment in 2015 where the evil thoughts in my head had overtaken the rational startup brain.”

As I read his story, I was incredibly proud of him for being able to talk about it and provide leadership for others. Then I read Lance Powers (founder at Sigmend – Techstars Class 68) post The Vital Role of Community in Mental Health Support where he talks about his bipolar disorder.

“If you would have told me 10 years ago that I would be writing a post discussing my Bipolar disorder for my friends, coworkers, and entire community to see, I wouldn’t have believed you. Thanks to the hard work of my local community in Boulder and Denver, I am not only comfortable writing this post, I am proud.”

Lance has two statements that encapsulate what I believe.

  1. “The problem is less about the disorder and more about the way we handle it.”
  2. “The one thing I know to be absolutely true is that a supportive community is vital to recovery.”

Lance points to Dave Mayer for paving the way for him to speak openly with the Mental Health in the Startup Realm panel Dave led at Boulder Startup Week 2016.

On Saturday, Amy and I participated in the annual BCH Foundation Gala which this year was in support of the BCH Foundation Mental Health Endowment. As part of it, we announced a lead gift for the new BCH Della Cava Family Medical Pavilion which will be used primarily for behavioral and mental health issues.

While more is coming on the work Amy and I are doing with BCH, for now, I’m going to end with the simple statement. I am incredibly appreciative and proud for all the insights, support, and bravery of all my colleagues and friends, around the issues of depression and mental health in general. Thank you.

Sonos + Alexa Strategy

We all know that Sonos is finally working on an Alexa integration. As I sit here listening to Atom Heart Mother on my Alexa (via “Alexa, play Pink Floyd’s album Atom Heart Mother”), I so badly want it to play throughout my house on our Sonos, rather than just on my desk via Alexa.

As more hardware companies start paying attention to revenue attach, following the lead of companies like Dropbox, Ring, and Peloton, there’s an obvious place for Sonos to do this. I hope they are thinking hard about it, rather than fearing being disintermediated by Alexa.

I’m very invested in both Sonos and Alexa, as I’ve got them installed in multiple places. Alexa is my desktop music system; Sonos is my house-wide music system. I pay subscriptions to a number of music services, including Amazon, Apple, Pandora, and Spotify. I’ve got them all integrated into Alexa, and most of them (except Amazon) integrated into Sonos.

I’d happily pay Sonos $5 – $10 / month for “advanced features” like Alexa integration. Right now I don’t pay Sonos anything, so $60 – $120 / year (and – a hint to my friends at Sonos – I’d prepay a year if you gave it to me for $50 – $100 with auto-renew) is easy to part with given how much value I get from my Sonos.

Now, I’d want to be part of “Sonos Life”, versus just paying for additional features. As a member of Sonos Life, I’d get all kinds of special happiness via Sonos on a monthly basis. Sonos doesn’t have to look very hard to figure out what to do since they – well – are central to music and have integrated many subscription services. Give me a free month of a service I haven’t yet activated. Or maybe special access to curated channels. Or live music that is syndicated from a different partner. Early access to new products. Fun promotions that all music lovers thrive on. Geez – maybe even a Sonos magazine (well – not really …)

Rather than being afraid of Alexa and integration, I wish Sonos would go all in before Amazon comes out with a connected speaker that causes me to consider ripping out all my Sonos systems and replacing them with Alexa’s …