"...none of it is easy" ✍🏔🔮
Says Trello's Michael Pryor. Here's him and other founders looking inward, then turning their gazes right back to name — and pass on how they’ve dealt with — the many, visiting startup predicaments.
Welcome to the 62nd edition of The SaaS Baton. A fortnightly newsletter that brings you three, hand-curated pieces of advice drawn from the thoughtful founder-to-founder exchanges and interviews taking place on Relay (curated with 💛 at Chargebee) and the interwebz. So, stay tuned!
The fleeting, in-between weeks are here yet again. Heavily freighted, this time, with a harsh resetting of the industry. Rendering the (already) perplexing task of compressing retrospections and projections ever more demanding.
We’re back again, too, with yet another collection of brief, introspective founder missives. All drawn from the Relay archives. Voices to hum along with as you muse over the past year, what has not yet come to pass, what has resolutely held its ground, and the hopeful, unbounded aspirations you still seek to chart.
In this edition, you’ll find the following instructive and inspiring pickings:
#1: Flodesk’s co-founder and CEO, Martha Bitar, describes how the day-to-day hurdles at a startup can conjure a worsening, perennially-aflame world and how she has learned to see through it.
#2: Bento’s founder, Jesse Hanley, on being aware of where burnout, for him, really stems from, and weaving a work-life-expectations routine that helps.
#3: inDinero’s founder, Jessica Mah, emphasizes the necessity of seeking outside perspectives especially when processing failures.
#4: Tray’s founder and CEO, Rich Waldron, on making decisions when advice, as it so often does, points everywhere.
#5: Trello’s co-founder, Michael Pryor, reveals the rocky, uncertain itinerary behind two decades of arriving at industry-defining products.
#1: “I would freak out less”
(From: Flodesk’s Martha Bitar) (Source: Relay)
I remember the first time our system crashed. It was a few months after launching and I thought that would be the end of our journey. We were down for about 4 hours and those were the longest.
The next morning, I woke up to about 12 customers telling their audience on IG stories that we broke the internet and that they had to join now. I was so focused on making sure that everything was perfect and would be so deflated every time we’d have one issue, one bug, one upset customer.
I would fundamentally change that approach.
I now know that sometimes things are going to happen, often things that are out of our control (like that time AWS was down) and what matters most is how we handle those incidents: did we communicate promptly and transparently internally and with our customers? Did we create a plan to get better in the future? Did we do a guilt-free and hyper objective retro?
That’s my big one. Would love to hear yours.
#2: “I get overwhelmed, stressed, strung out all the time — I think that’s normal and healthy”
(From: Bento’s Jesse Hanley) (Source: Relay)
I get overwhelmed, stressed, strung out all the time — I think that’s normal and healthy — but I find most of the issues stem from either me not having some key piece of knowledge (i.e how to scale a specific system) or not thinking about things from first principles (i.e the insight that our support could be done almost entirely on Discord vs. email and live chat was a huge one but felt VERY weird at the time).
Talking to friends, my wife, my dad or hiring help tends to be the unlock required to get out of whatever anxious loop I’m in.
As for routines most days are like this:
Wake up around 6-7am
Go to the gym (clean out Discord messages here)
Make breakfast
Work for 3-4 hours
Have a late lunch, go for a walk, do something fun whilst my food settles
Lock into an afternoon work session until dinner
Play video games whilst doing support until bed time
I’ll often also go exploring on my bike after lunch and find somewhere new to settle into. It’s nice to mix up my environment from time to time and I love finding a new cafe or book shop to work out of.
If I find myself really burned out I just wont work for a few days and forgive myself for it. I think this is the hardest part of being your own boss but I’m slowly getting better at it. After all, we all need rest.
Oh and a fun one I do often — some weeks, I divide a “40 hour work week” by 7 and just work a little every single day (inc. weekends). I find that’s super sustainable for me and slows things down a lot.
#3: “It’s very easy for us to learn the wrong lessons”
(From: inDinero’s Jessica Mah) (Source: Relay)
I think having an objective third party to assess helps a lot. It’s very easy for us to learn the wrong lessons or just not learn any lessons from mistakes, given how crazy workload in a startup can be.
As of right now I am leveraging two executive coaches, my therapist, and two more business consultants to help me figure out how I’ve screwed up and how I can improve and how we can improve the business.
I also have my former COO now as a board member who I trust to be objective in telling me what he thinks the mistakes have been and where we may be repeating mistakes because we didn’t post-mortem properly.
#4: “…one of the most paralysing things a founder faces”
(From: Tray.io’s Rich Waldron) (Source: Relay)
The conflicting scale of advice is one of the most paralysing things a founder faces, handled well it’s a rich source of information, handled poorly it’s a major timesuck.
I try to take everything as its own data point and ultimately process and come to a decision that is in the best interests of our overall vision, and the path to getting there.
An example I can think of (in early 2012) was the misrepresentation of the lean startup approach, as with anything it’s best consumed as a guide to support decision making but the emphasis at the time was essentially to create extremely lightweight prototypes of products.
This didn’t sit well with me at the time as I feel there is a balance between setting out your experiments correctly and having the conviction to commit to an idea that you believe it.
#5: “…none of it is easy”
(From: Trello’s Michael Pryor) (Source: Relay)
What seems consistent to you though was far from consistent.
Some times we built the right product at the wrong time (ten years ago we worked on remote work audio software that made virtual rooms for people and I think there are 4 startups I know of working on this today), other times it was the wrong product at the right time, or we got everything right but failed to market it correctly (we built screensharing tools before LogMeIn/GoToMyPc but pitched them as tools for customer support agents limiting our total addressable market).
Additionally, you wrote “first decade” but most of the “hits” you know about today were created after 2010 (whereas we founded Fog Creek in 2000).
Stackoverflow was a great idea that Joel had and an amazing product that Jeff Atwood built - but the reason it worked so well in ADDITION to the product was that both of them had spent a decade building up a reputation with developers through blogging. If that hadn’t existed, I don’t know if that product would have succeeded so well.
We also struggled sometimes trying to figure out how much longer to work on something before calling it quits (I get domain name renewals still for projects that we eventually stopped working on).
I know none of that is really an answer - but it’s just to say, none of it is easy.
If these reflections offered interesting/encouraging parallel moulds to think within, we’ve also put together a wider list in the following H&H piece:
Until next year,