Stacking the Bricks Podcast EP23 - "Everything will get easier if..." (Part 1 of a series)
30 min

In this episode…

2015 was the best ever for Amy's SaaS business Freckle, with $625k of gross receipts, and so far we’re on track to hit close to $800k annual run rate (ARR) before this year is out. Those are some big numbers, but we didn’t start out there, and it hasn’t been all smooth sailing.

In this episode we talk about the first of Five things I wish I’d known when I started Freckle, things that would have made my life so much more profitable and pleasurable.

Up first is "There is always another inflection point coming" aka the myth that "everything gets easier when..."

In this episode, we cover:

  • Why this original article seemed to catch on like wildfire
  • How to avoid post-launch depression
  • Ways to keep making money until your SaaS is paying the bills
  • Amy's favorite acorn squash recipe & Rudy's Rutabaga Rule
  • ...and a lot more

Listen up, and subscribe to get the next episode:
Teams are NOT 'just add water'

Transcript

Amy Hoy Amy Hoy: So I’d like to preface this with saying that I’m not crazy…

Alex Hillman Alex Hillman: Okay, I’ll grant you that for the moment!

Amy Hoy Amy Hoy: I’ll allow it. Alex the courtroom judge of my soul says he’ll allow that I’m not crazy – for now.

Alex Hillman Alex Hillman: For the moment.

Amy Hoy Amy Hoy: This line of questioning is okay.

Alex Hillman Alex Hillman: Back in March, Amy, you wrote a blog post that sort of caught on like wildfire. It was nice to see something like that and this post is a little bit different from a lot of the stuff that you’d put out recently in that it was super tactical about the SaaS business that you and Thomas have – Freckle. Do you want to talk a little bit about what it was?

Amy Hoy Amy Hoy: Sure. I called it, “Five Things I Wish I Had Known Before I Started my SaaS”. I think that was the title. It went through some permutations. I actually don’t think that it was tactical, I just went through five things that were sort of more deeper philosophical things actually – I think – that I wish I had known before I started Freckle in 2008, and by ‘I’ I mean, myself and my husband, Thomas.

Alex Hillman Alex Hillman: Do you have an idea of why that might’ve caught on like wildfire? Did you see any particular responses on Twitter or in our email replies that stood out to you?

Amy Hoy Amy Hoy: So I think a lot of people who were sort of established already with a Software as a Service business really liked it because I think there are some universal truths in there, and so they were like, “yeah, this!” basically. And then it spread among their network of people who are aspiring to do or be where we are.

Alex Hillman Alex Hillman: Cool. So this is stuff that’s learned, now, eight years into running Freckle as a business that applies universally across lots of kinds of businesses, but also applies back to lessons that you learned early on in the business.

Amy Hoy Amy Hoy: Yeah, it spans the entire gamut. Actually, the ironic thing about most of the lessons is that I didn’t just learn them once. I kind of had to keep learning them again and again, in various permutations thereof. So, it’s like, whack-a-mole, you think you’ve whacked the mole and therefore your problems are over, but it turns out there’s a whole bunch of other moles just waiting to pop up.

Alex Hillman Alex Hillman: Which is actually the first of really the lessons in it that we’re going to talk about today, which was that there’s always another inflection point coming.

When we were talking about this before we sat down today, the idea that there’s this feeling wherever you are in the life cycle of a business, or maybe just life in general, that if only that one thing would happen, everything would suddenly magically become easier and I feel like that’s just as true, if not even more true in business. And that’s sort of the point that you were trying to make there, right?

Amy Hoy Amy Hoy: I actually like that you called it a feeling because it’s a feeling, and it’s a lie.

When you start a business, you think, “Okay, if only I can hit this revenue amount”, or “If only I can grow my staff to a certain size”, or “If only I can attract this one major customer”, you think that everything is going to be easy. Or you think, “If I can just ship this part of book, or, “If I can just finish this section of the app”, or, “If I can ship this feature, or get this office”, you think that everything’s going to be easy.

Alex Hillman Alex Hillman: And even when those things are attainable, like you could do it, whether it’s now or in the next few steps, it doesn’t matter?

Amy Hoy Amy Hoy: Nope. You get there and then you realize it doesn’t actually make everything easy, that there’s something else that you have to do that will make everything easy. Then you get there, and you realize that everything’s not easy yet so you’re going to come up with another goal that if only you could reach, suddenly everything will be easy. It’s actually inflection points all the way down. There’s no point at which everything becomes easy.

Alex Hillman Alex Hillman: The way I always think about it is you don’t actually make problems go away; you just trade them for new problems. Even when you do a really good job of solving the problem, you’ve usually just traded up for a new, potentially bigger or harder to solve problem.

Amy Hoy Amy Hoy: “Life is suffering”, says the Buddha!

Alex Hillman Alex Hillman: Now that’s not to say that you shouldn’t set out to do it. That would be helpful to sort of rewind the clock, you know, seven or eight years towards the beginning of Freckle about what some of those early hypotheses were that “If we just did this one thing, it would be easier” were and a sort of how you pushed through it to actually get it done, and then what was the realization on the other side.

So from your memory, what would be one of the earliest examples in the arc of you running a product business that you were thinking to yourself, or you and Thomas are sitting there going, “Well, we just got to do this and then we’ll be in a better spot.”

Amy Hoy Amy Hoy: So the obvious first inflection point, or the, “do you think if we can just get to this point, everything will be easy?”, is launch. I didn’t actually sit there and think, “after we launch, everything will be rainbows and puppies”, or kittens - I don’t actually like puppies, “rainbows, and kittens, and everything will be easy and we’ll be rolling in money.”

I didn’t actually believe any of that. I think there would be work that would be continuing after launch, but I thought that that would be the last major stressful push, which is a whole load of horse shit!

We launched and of course, then there was more work. And actually, the thing about launching is if everything is building up to launch, afterwards, you launch, and you get like depressed. Not like full on, not real depression, but you spent all your mental energy looking forward to this point and then you’re there and you haven’t really thought too much about what do you do after that? And so, you don’t have a plan and also you’re kind of tired, so you kinda just want to roll around and grunt for a little bit.

Alex Hillman Alex Hillman: You also go from this stage of knowing exactly what you’re working on, sort of working step by step towards this goa – in the best-case scenario, and then all of a sudden it’s done and you haven’t planned the next step. In my experience, the worst thing you can do to yourself is not know what the next step is going to be before you get there.

Amy Hoy Amy Hoy: That is so very true. That’s what we tell our students now from personal experiences, that launch is only another day and that the work continues and you should have a plan for what you’re doing because when you don’t have a plan, then you’re inclined to sit on your butt and mope a little bit.

It’s so much easier when you’re working in isolation towards launch, to imagine all kinds of fantasy scenarios where everything is amazing and perfect and wonderful. As the old saying goes, “no plan survives contact with the enemy”. And in this case, the enemy is reality. So once your project’s actually out there, you have to deal with all kinds of things that you maybe didn’t anticipate.

Alex Hillman Alex Hillman: Including simply just keeping up momentum.

Amy Hoy Amy Hoy: Absolutely. Absolutely. I did not anticipate that. So that was an inflection point that didn’t fulfill its promise and of course the next biggest inflection point is being able to live off the revenue from Freckle. When freckle launched, we launched to a waiting list and our very first month of billings, we did $1,500, which is actually pretty, pretty good for a Software as a Service. But that’s what, $20,000 a year? $18,000 a year?

Alex Hillman Alex Hillman: Definitely not enough for two people who are previously relatively high paid consultants to replace your income, not even close.

Amy Hoy Amy Hoy: Correct, no we were living in Austria at the time and so we were earning in dollars and spending in euros, that wouldn’t have even paid our rent – which sounds really bougie now that I say it all out, but $1500 a month was nothing like enough to justify Freckles existence. I knew it was going to be that way, we knew we were going to grow it. And so, I thought that as soon as we could get Freckle to enough revenue to live off it, everything would be easy because in the meantime, we’d have to kind of hustle. We’d have to do consulting. We’d have to do other stuff to pay our actual bills, and essentially borrow money from those other endeavors to pay for Freckle.

Alex Hillman Alex Hillman: Gotcha. Gotcha.

Amy Hoy Amy Hoy: It’s tempting to imagine that if a pot of gold were to suddenly appear and you had all this money that suddenly everything would be easy, but if you or your friends have ever gotten venture capital, you know that actually only makes things worse!

There’s a fantasy that a certain revenue amount will make everything easy and it’s just not true. It took us a long time from my perspective, to get Freckle to the point where we could live off it.

Alex Hillman Alex Hillman: What was the time period?

Amy Hoy Amy Hoy: It was about 18 months.

Alex Hillman Alex Hillman: Okay, and we’ve heard that number before. Lots of friends who started their first SaaS with audience from scratch, 12 to 18 months to be hitting a salary replacing revenue goal.

Amy Hoy Amy Hoy: Yep. When I give a talk at La Conf a few years ago, I actually pulled a bunch of our business friends and asked them, “How long did it take to get to a hundred thousand dollars run rate?” and it was between nine and 20 months for everybody.

Alex Hillman Alex Hillman: So, remarkably consistent and that’s not to say that you can’t do it faster, but that there’s not a lot of things that you could do to get it faster, that wouldn’t just create additional problems somewhere else in the matrix of things that you then need to deal with, work on and so on.

Amy Hoy Amy Hoy: I feel like there are essentially laws of physics. It’s like when you’re in line at the grocery store and you think you’re going to change lanes and it’s going to go faster. It really doesn’t, you cannot make the grocery lanes go faster.

Alex Hillman Alex Hillman: It’s like an internal psychology, it’s the same thing as pressing the button to cross the street. That button probably doesn’t actually do anything. It’s there to make you feel like you had some sort of control over it. I think that’s what you’re really talking about here is all these inflection points, what they do for us is they are a moment where we feel like – and it goes back to that like – feels like we get to exert control over something, it’s temporary but it fulfills that feeling. Once the feeling is done, then you’re sort of left to face reality and say, “well, I felt like I was in control, but was I really? I don’t know if I really was?”

Amy Hoy Amy Hoy: Yeah. I mean, you’re in control of a lot of things, but you’re not necessarily in control of the outcome.

Alex Hillman Alex Hillman: Right. Exactly. You can’t control whether or not people sign up for your service.

Amy Hoy Amy Hoy: No you can’t, you can only try to do all the right things and it doesn’t necessarily work the way you want or as fast as you want. I feel like the sales process – and I don’t even mean like high touch sales, I mean, the time it takes from someone to hear about you, go to your website, read your website, decide they’re going to try it, and then actually buy it and implement it and all that stuff. That takes time, no matter how much money or effort you throw at it.

Alex Hillman Alex Hillman: So we’re just talking about pre-early stage in Freckles existence, where even out of the gate, you had a measurable success; a product that’s billing, $1500, $1,800 a month. Not enough to replace your income, but that is the next major goal and you were saying that you were doing other things along the way to sort of fill in the gaps and pay those bills, so that you didn’t have to go to consulting? Talk a little bit more about that.

Amy Hoy Amy Hoy: We consulted for a while. It wasn’t until a bit later into the process of having Freckle launched to the world that we – and by we – I mean, I, decided I could not consult anymore. I knew I didn’t want to consult anymore, but I thought, “Ah, I’ve been doing this for years and years. I can tough it out.”

It wasn’t until December 2009 that I decided that I was totally done and would do anything I had to do to not consult anymore. But by that point we had created a couple other sort of product-y type things to help sort of plug the gaps in our income from Freckle. So, we had done a book called JavaScript Performance Rocks! and we had also been doing JavaScript workshops.

We had done the first couple of workshops live at a venue and sold tickets and seats, and literally had to fly there to present a couple of cases. We rented our own venue and we’d also done it at a couple corporate locations, but then we realized that was just not sustainable. And so we started doing it online every month.

Alex Hillman Alex Hillman: Gotcha. Gotcha. Gotcha. So that’s adjacent to Freckle in a lot of ways, a totally different audience?

Amy Hoy Amy Hoy: A totally different audience.

Alex Hillman Alex Hillman: So it’s really purely working on plugging the financial gap entirely. Within building those, you mentioned before, it’s like there’s inflection points all the way down. Were there any inflection points inside the JavaScript Performance Rocks! and the JavaScript workshops that while people are working on these financial-gap-plugging products they might run into as well?

Amy Hoy Amy Hoy: I think it’s in large part, the same inflection points. So, we thought that once we had developed the workshop itself, that everything would be easy or that, “Sweet, we sold beta copies of the book” and that wasn’t like…hold on, dialing back the memories here…insert a montage with dates and clocks running backwards…So that was, I believe we shipped the beta version in January, 2009 because it was right before we went to New Zealand for Web Stock, it had to be January or February of 2009.

Alex Hillman Alex Hillman: You said a beta version? So incomplete or edited?

Amy Hoy Amy Hoy: Incomplete.

Alex Hillman Alex Hillman: I got it. Just for our listeners sake, where did you draw the line in terms of, “Okay, we’ve got to get this out there”. What was missing? What did it have and what was missing, for it to be an alpha or a beta?

Amy Hoy Amy Hoy: I don’t remember! It was not complete though. What I do remember is spending long nights working on the book after that, so I think there were multiple chapters there and also laid out, type-set and in design, which by the way, don’t do that. But there was a lot of missing content. Thomas was still running benchmarks and tests and it wasn’t all beautifully written. There was definitely at least half of the book not there.

That is how the book publishers that do this, the technical books, they ship beta books, they’re not complete. Beta is really a misnomer, it’s really an alpha. It took us about a year to finish it, on and off.

Alex Hillman Alex Hillman: Okay, so we’ve got inflection point one - we just need to create this book. You create the book in this alpha forma, you ship it, you’ve made some sales, that gets things going

Amy Hoy Amy Hoy: Yeah, we made a lot more sales than we thought, actually.

Alex Hillman Alex Hillman: Which is great. But now you’ve pre-sold a bunch of copies of a book that’s not done?

Amy Hoy Amy Hoy: Yep, that was stressful. That’s why I don’t recommend doing that. Our students often were like, “well, this internet celebrity says to presale something, just test the market for it”, but then no one talks about the psychological weight that you have from having sold something that doesn’t exist and having to essentially backfill that work.

Alex Hillman Alex Hillman: And talking about lessons that need to be learned with multiple times – how many times have you and I had done that with 30x500? I can count at least two, maybe even three times in history that we’ve done that.

Amy Hoy Amy Hoy: Yeah. That’s more like four or five…

Alex Hillman Alex Hillman: I was being conservative!

Amy Hoy Amy Hoy: You guys should see my face right now! I think I must have a hunted look. Definitely had to learn that a bunch of times! It’s so tempting and expedient to be like, “well, I have the outline and I know everything’s going need to get done to sell this. I’m going to sell it now and take the money.” Sometimes, you kind of have to do that, but it is a mistake. Better to ship a smaller product that’s done-ish than to get pre-sales for something that’s huge.

Alex Hillman Alex Hillman: So inflection point being, we just need to finish this thing?

Amy Hoy Amy Hoy: If we just finish this, everything will be easy. And so actually I thought that selling the beta copy, then it would essentially fund its own development and then that would be easy. Actually, I mean, we finished it. A lot of people never finish their books. We did finish it and we finished it in a normal publishing timeline – to finish a technical book inside a year is pretty good, but it was a weight on me the entire time. It was like, “Ah, I have to do this”. Instead of being excited to finish it, I felt like it was all duty and I don’t like that feeling.

When we did finish it, that was great. However, that doesn’t continue to sell copies, as we all know. Launch day is so overrated for selling, then you have to create your marketing toolkit and you have to create your marketing content and so on and so forth. We actually didn’t do a very good job of that, the amount of money that JavaScript Performance Rocks! made, I think was really abbreviated compared to what it could be if we had done it correctly.

Alex Hillman Alex Hillman: So you’ve got that and you’re past that inflection point and now you’re using the money from JavaScript Rocks! and the workshops and things like that to help fund development work in Freckle, Is that right?

Amy Hoy Amy Hoy: Not exactly. So ,we weren’t literally taking JavaScript Performance Rocks! money, and paying somebody with it. We were essentially using it to buy our own time, to continue working on something that was not paying for itself.

Alex Hillman Alex Hillman: So that’s investment mindset in action, right there?

** Amy Hoy**: Investment mindset. Also, I’ve written about this under the heading ‘Be Your Own Angel’, is to come up with the money that you need to free yourself to build the thing that will actually become your business.

Alex Hillman Alex Hillman: Even in relatively small components. So you’re not talking about buying all the time you need, it’s buying just a little bit at a time.

Amy Hoy Amy Hoy: I honestly think that having all the time in the world means that you’ll never finish.

Alex Hillman Alex Hillman: That’s a really good point. That’s a really, really good point.

Amy Hoy Amy Hoy: If people out there is listening to this podcast thinking, “Gosh, if only I had six months of runway to quit my job and do nothing but work on my amazing Software as a Service, I would launch it and have all this money” – you’re fooling yourself. What will happen when you have infinite time is your product will keep growing and then you will not launch it. And if you do launch it, you’ll discover that it takes nine to 18 months to come up with a salary replacement. So, don’t do it!

Alex Hillman Alex Hillman: Without inserting myself into the story or distracting too far, although I’m actually going to do that…

Amy Hoy Amy Hoy: Just stop apologizing and just do it!

Alex Hillman Alex Hillman: One of the things that I’ve done in the past for myself, and I’ve also advised other people to do is instead of trying to replace all of your expenses at once, break it down into smaller components. So, what would it take for you to ship and sell something that replaces your cell phone bill in recurring revenue of products?

Amy Hoy Amy Hoy: That’s awesome! You’ve never shared this with me, and I love that!

Alex Hillman Alex Hillman: Something super tangible – we’re talking about under $200 a month. You can absolutely ship something that makes under 200 bucks a month, and once you’ve got the confidence to have your cell phone bill paid for, then move to your car payment, move to your home utilities, you work your way up to the bigger expenses and then before you know it, all your expenses are covered, but you know exactly what it takes to keep adding to it, that’s your gravy.

Amy Hoy Amy Hoy: That is awesome! That is stacking the money bricks.

Alex Hillman Alex Hillman: I’m stacking the money bricks! The beautiful thing about that is, inside each one of those components, you also have a bunch of things you can control, or you can look at it and say, “All right, there is an expense that is maybe out of my reach, but I can break it into smaller parts, or maybe I could even reduce it.”

I’m sure not telling you that you need to reduce costs in order to reach them but once you’re within a smaller contained component, it’s much easier to look at that critically than when you’re looking at an entire month’s worth of expenses all as one unit.

Amy Hoy Amy Hoy: Yeah, I think that’s an excellent point. I think people who are not familiar with running their own business, they haven’t even thought of that. It’s like the way that I, and you, and, you know, Brennan and all of our business friends think about money is, “There’s this thing I want to do, how can I pay for it?” Many of us have launched a small product or worked on something in order to pay for something that we wanted to do or that we needed to pay for. It’s not a familiar mindset to people who are used to working for a living at jobs.

Alex Hillman Alex Hillman: And all of that being said, even that approach has an inflection point, because then when you get good at paying for the things you want, you start wanting new things. I’m – compared to a lot of my friends – a pretty serious minimalist in terms of things that I have, that doesn’t mean that I don’t find new ways to spend money. I just find new ways to spend money.

Amy Hoy Amy Hoy: Whose law is it that work expands to fill the time available?

Alex Hillman Alex Hillman: I don’t know. We’ve talked about it before on the show though.

Amy Hoy Amy Hoy: I feel like it’s Parkinson’s law.

Alex Hillman Alex Hillman: I think that’s right.

Amy Hoy Amy Hoy: There’s too many fucking laws named after old dudes. I think it’s Parkinson’s law, that work expands to fill the time available and I think the same thing is true about lifestyle or aspirations is that you buy the house and then you love your house for multiple years. And they you’re like, “Now I need a cabin!” And by you, I mean, me! I bought a cabin in the woods and the mountains and it was a stressful period because of the money – mortgage brokers are crazy, but, that was definitely a motivator for me to work on the new 30x500 – one of many.

Alex Hillman Alex Hillman: So to pull us back into the article and these inflection points in your story. Let’s talk maybe something a little bit later stage in the story more recent inflection points because you have a fairly mature business, creeping up on a million dollars a year in recurring revenue.

Amy Hoy Amy Hoy: It’s not super close to a million dollars a year. It’s not quite $700,000 a year right now.

Alex Hillman Alex Hillman: Getting there, but growth, you’re on a trajectory to be able to get there. That sounds awesome. Lots of people would love to be in that position, but once again, problems don’t go away. You just trade them for new problems.

Amy Hoy Amy Hoy: Yes, it’s Rudy’s rutabaga rule.

Alex Hillman Alex Hillman: I know we’ve talked about that before, because that’s the kind of thing that hits my brain and goes, “You’ve heard this before, and the last time you thought to yourself, that’s amazing! How have I never heard that before? What is it?”, So I’m going to play Alzheimer’s patient right now and say, “Amy, that’s amazing. I’ve never heard of it before, even though I’m pretty sure I have. What is it?”

Amy Hoy Amy Hoy: Well, it helps that you don’t actually remember what it was.

Alex Hillman Alex Hillman: I legitimately don’t – as soon as you tell me, I might remember, but I’m going to go into this assuming that I don’t.

Amy Hoy Amy Hoy: Rudy’s rutabaga rule – which you must say like that because otherwise your tongue get all tied up – is from The Secrets of Consulting by Gerald Weinberg. He tells a story, an apocryphal business books story, you know how it goes, about a young man who works at a grocery store and he’s just got a new job and he’s super in to showing how useful he is to his boss and being really efficient. His job is to stock the produce and so he goes to his boss because he’s noticed something and he says, “Boss, rutabagas are a poorest performing produce”…

Alex Hillman Alex Hillman: I just remembered this story, but keep going…

Amy Hoy Amy Hoy: And the boss is like, “Yes, and?” and Rudy says, “Well, if we get rid of rutabagas, our overall profitability will increase because people just really don’t buy rutabagas.” His boss who has clearly been in the grocery store business for a long time, says, “Yes and then what will be our lowest performing produce?” So, you can get rid of rutabagas, but then I don’t know, acorn squash might be your next worst product.

Alex Hillman Alex Hillman: Who the hell buys acorn squash?

Amy Hoy Amy Hoy: Actually, a lot of people, acorn squash is a terrible example. They’re very popular right now. They’re trending on Pinterest! Oh yeah! Acorn squashes were totally big this past fall season. Alex is just shaking his head at me.

Alex Hillman Alex Hillman: Things I didn’t need to know today!

Amy Hoy Amy Hoy: They taste great! You can stuff them with sausage and quinoa and it’s incredibly hipster and also delicious!

Alex Hillman Alex Hillman: We’re pivoting this into cooking show.

Amy Hoy Amy Hoy: The thing is you can eliminate your biggest problem and then your next biggest problem will suddenly be your biggest problem. It is problems all the way down. You cannot escape problems, there will always be a biggest problem. The only question is, is it tolerable or not, or would the next biggest problem be a better biggest problem?

Alex Hillman Alex Hillman: I think that’s a really good way to think about it, and I was thinking about this in terms of a lot of the things that are going on with the new Indy Hall build too, I’m looking at the problems and going, if we’ve got a bunch of bad options, what’s the best of the bad options – I have to choose at some point and I’m worse off if I don’t choose it all, so what’s the best of the worst? Let’s go, let’s make it happen.

Amy Hoy Amy Hoy: Absolutely. Nothing quite like a construction project to teach you where you will compromise. My rule of thumb that I came up with after working through our office remodel, which was fairly extensive, but not as big as yours. Also thinking about what we’re going to do to our house.

When I think about the construction that we’re going to do to our 1740s row house – it’s extremely stressful to me because I feel an obligation to protect the house as much as possible because it’s going to outlast us. So, the solution – the rule of thumb – I came to was, if I bought it like this proposed idea, how would I feel about it?

When you start off doing something new, you think it has to be perfect. We have to get to this point; it has to look like this. It has to be like this, it has to earn this much money. It has to have these features or whatever, from zero to this imaginary perfect place. When actually, something that’s like 60 to 80% there – if you had that, you would be really happy.

Alex Hillman Alex Hillman: You can always build on it and evolve it and grow it. But if you never get to that starting point, you have nothing to build on top of, you have nothing to grow.

Amy Hoy Amy Hoy: Nothing to go, right. So, it was a hard lesson to learn in the sort of renovation area of life but we’ve been telling our students forever that to run a business like this, you have to be willing to live at 80% all the time. Nothing is ever done. Even people – they make a physical product and they ship it and there are still issues. There’s always an issue. There’s always something could be better, there is no perfect product. There’s no actual ‘done’. You think, “if I only get to an inflection point, I’ll be done.” Well, great. You’ll get to that inflection point and then standing on that local, maximum peak you’ll look around and think, “Oh, well there’s a higher peak”, or, “Oh, these shoes didn’t really work really well climbing this peak, I need better footwear.”

Alex Hillman Alex Hillman: This actually translates to even very, very large operations. I was just listening to an episode of Planet Money about the technology that UPS uses to shave pennies at a time that add up to hundreds of thousands and millions of dollars in savings – in their business – in time and fuel costs and operations and turnover. It was a really, really interesting way of looking at how – even the changes they make are small and incremental, but they compound and they add up in a big way.

Amy Hoy Amy Hoy: Absolutely. Office space.

Alex Hillman Alex Hillman: It’s so interesting how that pattern continues to grow. I think the most important thing here is realizing these lessons and learning these lessons early on and actually embracing them and making them part of how you operate and make decisions. It means that as you get bigger, instead of expecting things to somehow get easier, instead, you just get better at looking for these kinds of trade-offs and making an analysis of saying, “how do I trade this off in the most valuable way that I’m capable of, that I know how do?” and being okay with it not being perfect, but being better in the right direction.

Amy Hoy Amy Hoy: Yeah. If you don’t learn to be okay with it not being perfect, you are going to want to die all the time, you’re going to be miserable and wonder what’s wrong with you and be unhappy, and there’s a recipe for unhappiness.

I think incremental improvement – that’s what we preach, right? The stacking the bricks, that’s right. Getting better at this and that and making a little bit of money here, a little bit of money there and growing that over time because if you don’t start stacking that first brick, because it’s not perfectly rectilinear and not 100% platonic smooth surface on all sides, you will literally never make a brick.

Alex Hillman Alex Hillman: Yeah, you can’t get to brick 10, unless you start with brick one.

Amy Hoy Amy Hoy: Yeah. Sidebar - I recently learned that bricking in certain slang-English means shitting so…

Alex Hillman Alex Hillman: Relevant side note!

Amy Hoy Amy Hoy: Yeah! So, I mean other inflection points with Freckle or our products, like I’ve only, I finished this version of 30x500. It will be amazing and everything will be perfect and all students will succeed. It turns out that’s not true.

Alex Hillman Alex Hillman: We’re still learning new ways of what we have to add in terms of support structures and communication, and also now that we’ve got a product that makes it easier to launch, we have to completely change the way we launch.

Amy Hoy Amy Hoy: It is really true. It literally never ends.

Alex Hillman Alex Hillman: But if we go into it with that mindset, and instead of being surprised by it, we say, “This is going to be there” - and this has mental gymnastics, and I’ll be totally honest upfront and say that – absolute mental gymnastics. However, if you choose to go in and say, “I’m going to do this and know that there’s a new challenge around the corner”, instead of being surprised by it – and I think it’s the surprise that lets it turn into an angst.

It’s the same thing as the post-launch depression. It’s the surprise that there’s nothing certain to do next. If you know there’s nothing certain to do next, you can do something about it even in that moment, but setting yourself up to remove those surprises I think that’s just a universally valuable approach to decision making.

Amy Hoy Amy Hoy: You cannot change the reality that there is always another problem. The only thing you can change is yourself.

Alex Hillman Alex Hillman: Very, very Zen!

Amy Hoy Amy Hoy: I know, but there’s a reason that is at the core of every philosophy basically ever. Including nihilism and all religions!

Alex Hillman Alex Hillman: So as we wrap up, I’m wondering if in the most recent years of this mature business, have there been any particular inflection points that were challenging or surprising to you?

Amy Hoy Amy Hoy: This sort of gets into the next part of the essay, but I believe I’m very much not alone when I thought that being able to hire staff would make everything easier, having the money to be able to hire a team, to help outsource some of the work did not work for me.

Alex Hillman Alex Hillman: Teams are difficult. People are challenging.

Amy Hoy Amy Hoy: People are challenging!

Alex Hillman Alex Hillman: You’re not just dealing with your own internal psychologies is like we’re talking about. Now you’ve got the psychologies of a bunch of people and their interconnectedness and things like that. So why don’t we treat that as our closing point for today’s episode and think about for the next episode, talking about the surprising challenges of hiring a team while building a SaaS business?

Amy Hoy Sounds good to me!

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