Funny thing is I have known about some of these companies since about a few years. I distinctly remember seeing Ghost's revenue (around $40K) and thinking, "umm.. that doesn't seem much to go around five people."; watching Hubstaff numbers (which was ~$80K/month, I believe), and saying to myself, "that's a very niche software. Would it ever go to make revenue that justifies expenses of a team?" (I think the CEO mentioned that he had taken zero salary since starting the company)
I am amazed how far they have come. So, a lesson learned well: If you're starting a company, you're fighting a long, hard battle against pessimists like me.
Don't want to personalize this but, since we're mutually reflecting on the sociology of talking about running a company and dealing with external perceptions: the specific names of the pessimists may change but there is absolutely no level of success at which folks will stop saying "Pfft, that's not a real business."
I think the takeaway for founders is being prepared for this and learning to not weight external pessimism all that highly, particularly not of the low-brow dismissal variety (what are the general odds that someone who has known about a business for 180 seconds has found the fatal flaw). For the broader community, I think the takeaway is intentionally being almost unreasonably supportive of people building things.
As a pessimist for the first 30 years of my life, I've finally realized just how little utility there is in being negative. On the flip side, being positive:
1. Helps you get more done
2. Helps other people get more done
3. Makes you more friends
So I'm going to chime in as a perpetual pessimist.
I've found tremendous utility in expecting negative outcomes. I'm wording this very pedantically, because my father and I used to argue past each other for hours re: "being negative vs saying something is negative."
Perhaps it's just that I've been in Ops/distributed system maintenance and development, but I've found expecting a worst case/pessimistic outcome pretty much always leaves me far more prepared, and more often than not, ends up being more predictive than my optimistic peers.
This has held true across time estimation, black box complexity, political outcomes, social overhead, model performance, outage frequency, pretty much every situation I can think of where I had to do long term planning in recent memory I feel well served by attacking from a "how is this going to go wrong/what are our blind spots/what do we do when this fails" angle.
The primary reason I make the (socially risky) statement of this is that I very often get (no hyperbole) guilted for being a pessimist, even when taking nontrivial effort for the negativity to be actionable and focused. It took me a good few decades to learn how to wrap my words and beat around the bush, (I was told by managers early on in my career things verbatim such as "you need to toe the party line more.") but even now that I experience almost none of the social friction that I used to, I find myself frustrated by the inefficiencies and gaps in this manner of communication, and find these gaps almost immediately ameliorated when I'm on teams which have a much more pragmatic approach towards being pessimistic.
Simply put, I had a very different experience than you, I've found an fixation on "being positive" to _massively_ impede Just Getting Things Done, and I've actually had much more luck bonding with coworkers over shared frustrations/issues and building lasting friendships like that than in teams where we're all wearing "let's be happy" masks. (This is a strawman, I don't expect you were arguing to this extreme, but I often find it manifests in this way in larger companies and as such want to try and argue the benefits of other angles of approach)
I think there's a happiness vs. success tradeoff with optimism vs. pessimism, and it works in counterintuitive ways.
In my experience (both personal and with close family members), pessimists are happier but less successful than optimists. They're happier because if you already think the worst is going to happen, it doesn't take much to exceed expectations. It's the old "happiness = reality - expectations" saying: set expectations at zero and anything that happens makes you happy. There's also an aspect of taking control of risks and actively working to avoid them that you mention, which makes near term, immediate reality more likely to go their way.
They're less successful because if you believe that most risks will turn out badly, you are less likely to take "leap of faith, have no idea what's going to happen" risks. Why would you, if the outcome is already known and will likely be bad? But in today's economy, many of the great successes come from taking big risks where you don't know the outcome and nobody else has the balls to try them. (This is a feature of markets: gains accrue to the people who supply what nobody else is willing to supply but which many other people demand.) So pessimists tend to make great technicians but shitty visionaries, while optimists tend to make great visionaries but shitty technicians.
I've fallen on both sides in my career. I've found my biggest successes usually have come from leaps of faith that I was was willing to suspend my "This is totally gonna blow up in my face" belief for, but those opportunities come from and must be followed by periods of actually thinking about and managing all the ways that it could blow up in my face.
As a fellow pessimist, I thank you for such a well written piece.
To add to this: I'm pessimistic that any of my individual efforts will succeed... I have 0% doubt that if I keep trying eventually something will work for me.
I see everything else the same way. 99% of the time people are wasting their time. Though I'm not a Debbie downer, I tend to keep this opinion to myself.
In general it is harder for me to cut loses than it is to join new projects. So I guess that's also why pessimism works for me.
As someone once said:
You've got to know when to hold 'em
Know when to fold 'em
Know when to walk away
And know when to run
You never count your money
When you're sittin' at the table
There'll be time enough for countin'
When the dealin's done
I think eventually the point is "just carry on doing what you have to do and get things done regardless of what happens". a stoic, stable and confident mentality which entails a lot of planning and calm decisionmaking helps. Either blind optimism or blind pessimism would be to the extreme and counterproductive.
Thanks for talking about your experience in detail. There are many sides to this question and it's helpful to have a variety of well-articulated perspectives.
My biggest successes have come from teaming up with people like you and people who are way more optimistic than me and cover both sides and balance them well.
Love this comment. I do a lot of self-reflection and one thing I've realized and still trying to change about myself is that I'm a huge pessimist and those 3 things you listed are things I'm terrible at.
I had a friend who said the same thing about Google when they first IPOed. His suggestion was that they should take their new cash and just go buy a real business so they're real (specifically suggested AOL Time Warner). This was a trader at one of the world's biggest hedge funds. He went on to have a very successful career in finance nonetheless. It's hard to make predictions about things we don't understand. A lot of our expertise isn't transferable to other domains and we sometimes overestimate the generalizability of our expertise.
Doubters and cheerleaders are both likely to be wrong and there is also so much you can't predict about the boarder environment businesses must operate in. Sometimes even the best of us fail and the most incompetent of us get lucky once in a while.
I'm curious how it breaks out to lower tiers. How impressive is $20,000/month, $100,000/month etc. and what percentage of SaaS get there, how long it takes, etc. Is there anywhere that has a nice table of that data for tech SaaS? That's the kind of info that would be quite fun and informative to look at.
Does it really matter? There are a thousand reasons why businesses fail. Also, $20,000/month can be quite impressive, if you earn this for yourself and live somewhere with low costs of living.
Seeing those numbers is just entertainment. If you hit your number, you figure that it doesn’t matter if it’s impressive for others.
This is a bit off topic of the main post but do you plan to add Twitter login to the Android app? I can't use it to access the books I've purchased because I logged in to the website with my Twitter account when I made the purchases but can't do so on my phone.
Been following Gumroad for a while! Would love to add it but I don't recall seeing anything like interviews or "making of" posts anywhere – I tried to add a little more than revenue numbers here.
As far as I understand creativetim.com uses gumroad for payment processing. Creative team has self-reported their revenue to about 1M per year. So kind of 20% from a single customer
That's a very interesting insight. I'd love some verification, but with the openness of all these numbers, it seems very plausible. If 20% is truly from a single customer, that seems very fragile, no?
Similar to this, I was looking for some inspiration about a landing page, I've found the top 1000 SaaS (https://saas1000.com/) with some data about them: Location, employees, 6 month growth and if they have some investisors.
I see Buffer in the list with 100+ Companies with Remote Open Positions and I guess that important to see real information about a company that you'd like to be hired.
When you see Key Metrics of a company, you know how you can grow there and help it to be better.
I made an open revenue page for https://geocode.xyz/open
It is hard to keep it up to date when there are 4 different revenue sources, but it is a good signal to send to customer s saying "hey, we are growing, so you can be more confident working with a company that's going to be still around down the road."
Yeah, a part of "open" community is to provide MRR, or at least Annual revenue, so potential makers can have an insight on how business in a given niche performs.
If you want to read content and engage in conversation with folks who boot strap this is a site I found on hacker news a while back that’s been good: https://barnacl.es
Thanks! Tried to keep it as clean as possible, which turned out good I guess. It's plain bootstrap for the front end, built and served by a SSR Nuxt application.
Yeah was on the edge thinking whether to include it or not, but pre-acquisition Courtland posted some really useful stuff about how he grew it. Felt it was a shame not to include, especially since it's very helpful.
I am amazed how far they have come. So, a lesson learned well: If you're starting a company, you're fighting a long, hard battle against pessimists like me.