Practical Founders Podcast
#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head
26 Dec 2025
Chapter 1: What are the most important questions for SaaS founders to consider for 2026?
Everybody's doing really hard things that are practical founders. I know you are too. And the question isn't what's the perfect growth rate and what's the perfect planning process for you right now. The question is, are you lined up to do enough of the most important hard things in your business next year? That includes you in your business as a founder.
to make the kind of progress you want to make along to the vision that you have of the company. So there's all kinds of ways to do it. You can go fast or slow, or it could be an invest year or a rebuild year. It could be a steady year. You can choose your growth rate, your profitability, and all of that. Hey, everybody.
Welcome to the Practical Founders Podcast, where every week we hear an amazing story from a serious founder who built a valuable software company and did it without big funding. I'm your host, Greg Head. And this week, I've got an end of year 2025 message for you. It's holiday time in North America. And in Europe, for many people, it's end of year. Things are winding down the calendar year.
It's a time when all entrepreneurs have a little bit more space to think, unless it's a seasonal spike. It isn't for most entrepreneurs. And some of you have gone through planning processes and sketched out 2026 and all the different ways you can do it or not do it. It doesn't really matter. But we're thinking about what's next in our business.
This last month in my Practical Founders CEO peer groups with about 40 founders from all over North America and Europe. We spent time looking back at what happened in the business this year and everybody's business, everybody, all the CEOs reported to each other in the five different groups. Here's where we ended up with revenue. Here's where we ended up with growth. Here's how I feel about that.
Here's what I'm thinking about next year. Is it a big year, a small year? Here are the main initiatives. Here's what success would look like next year. They're all making it up. I know you're making it up. And the question isn't, is a 20% growth rate good or 100% growth rate better? There were founders in the group with 100% growth rate that were disappointed because they thought it'd be higher.
And those with a 5% growth rate that made a ton of changes in their business and improved things drastically and were ecstatic. So there's many ways to think about it. There's no judgment. And today we're not talking templates or quick fixes or simple ideas. This is the natural condition of the entrepreneurship game, especially for practical founders. We do hard things.
And I'm really proud of the founders this year in the Practical Founders peer groups and many that I talked to and, of course, talked to here on the podcast that they got through a lot of hard things last year. Sometimes it was a personal issue that they had to deal with.
that made life difficult for them sometimes it was something external to their business headwinds and sass or their market or competition ai falls into that this makes things a little cloudy sometimes it's stuff inside their business sometimes it's stuff inside their heads that we make progress in some areas of the business and we don't make progress in some areas some things we didn't see
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Chapter 2: How should founders evaluate their focus on hard things in their business?
We as founders, we have superpowers. We're really good at stuff. It's easy for us. It happens in the business. It's the day-to-day that we don't have to think about too much. And many of you have businesses from, let me say, 2 to 10 million that are building a factory and more and more gets in that we just do this every day kind of thing.
So when we talk about planning processes and thinking about the next year and looking back to this year, we're talking about moving forward. The most important hard things, not everything. So it's the hard stuff that gets us and gets us stuck. It gets us, punches us in the face and creates headwinds for our business, makes things more expensive, makes that journey longer than we expected.
And, you know, I've been doing this a long time and I've spent time with literally 3,000, 4,000 founders. Now I'm inside 42 software businesses every month with my practice on peer groups. founders. And I almost have never heard that a founder tell me we got there faster and easier than we thought. So there was a lot of success, a lot of happiness.
Everybody made progress this last year, CEOs in my peer groups, in their business. But there was different versions of it was a good year, it was a hard year. We were... you know, below expectations by this much or a lot. The good news for all practical founders is you don't have big VC funding signed up for big goals. And if you miss the goal by a little bit, it's total disappointment.
You kind of got a gun to your head. And if you don't keep up with that it's an all or nothing proposition. So for better or worse, practical founders survive long enough to come at it again and do it again next year. We do hard things and that's what gets businesses up and running. But to continue, the game changes as your business grows and life goes on. So I want to share five useful questions
for you to think about your next year. Maybe that's your next quarter. Not everybody plans in years, which is just fine. So when I talk about year, we'll just say it's next quarter or your next sprint or your next time phase. I like to think about generally in the year and then prioritize for the quarter and what I do.
But if I'm running a bigger business, which I have with hundreds of employees inside a public company and big budgets and all that stuff, it's a three-month detailed planning process to say, here's what we think the priorities are and so forth.
So, by the way, the most advanced planning processes that take the most time, the EOS planning process, all the other strategy planning process doesn't guarantee that you're going to do better than somebody who doesn't have a lot of planning process, but makes the most progress on the most important things, generally on the hard list. to improve their business.
So let's talk about the five things, five questions that are useful for you. Again, they're not templates. I just want you to... hear what's going on. These are laws of nature. This is the human condition, the struggle, the conflict, the hero's journey. I'm not creating anything new here. Shakespeare's talked about all of this. Every strategy book has talked about it.
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Chapter 3: What changes should founders plan for in their business this year?
But it's the things we focus on to make the most progress in the business. And generally, it's the new and hard stuff that we spend the most time focusing on that isn't already in the business here. The real question is, are we focused on the right things? Now, most founders say we have a planning process and I think about these things. I'm pretty good at what I do and so forth.
But I'll ask you just to reflect and maybe think a little deeper about this. I've had thousands of these conversations with founders. And
Almost always, they get a little different perspective when I hear their story, when I repeat it back to them, when I give them a different perspective, when people hear it from different founders and different peer groups, you know, they kind of squint and say, oh, I didn't think about that in that way.
And especially if you look back at this year, you know, really ask your question, ask the question, did we focus on the right things this year? Did they move? Were we surprised what got added to the list this year? Is there something we would have done differently? And, you know, we have confidence about this and fidelity that we're working on the right things.
That's kind of the job of the founder, CEO. One of the main jobs is to make sure we're doing the right things. everything else you can delegate. But that's one of the things that CEOs are responsible for, to make sure we're focused on the right things. So we have some confidence about that. But we also have humility.
I've been doing this a long time, looking at that quarterly annual planning process, whatever it is, and realizing that we never crushed it, you know, every time for everything that And almost always we get to the end of it and there was surprises and some learnings and we didn't get as far as we thought and our expectations and our optimisms a little higher. So maybe just having a think about
Really, are we focused on the right things in the business next year? Again, there's all kinds of people that have very detailed planning processes. And I'm, you know, if you've been part of a big organization, you know what that's like or have created a big organization. The bigger that is, the more that planning and alignment and budgeting and coordination is as important.
and also creates the challenges that big companies suffer with. And there's all kinds of ways to do it. There isn't one rate to do it. So maybe if you look back and you look forward to whatever the next period is to think, what are those things? So I know founders who say a very detailed process. I thought a lot about it. Here's what's going on. Here's the data. Here's what we think about that.
Here's where we want to be. Here's what we do next. We align the team. We figured it out. We prioritize the roadmap and go to market and what's more important in the business and new initiatives and new products. And, yeah, we put a lot of thinking into that. But, you know, just have a think about that at the end of this year while things are quieting down and say, am I missing anything?
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Chapter 4: What type of help do SaaS founders really need to succeed?
This is the beauty of the founder magic and entrepreneuring and starting software companies and practical founders is the superpowers and strengths and weaknesses of your company often reflect the strengths and weaknesses of the founder. So maybe one of those areas to look at to say, I'm really good at this. We'll talk about this in one of the next questions here.
So you might just double check your blind spots, double check what's really happening out there, your biases, so forth. If you have tendencies that say, I'm always like this, then you might look on the other side of that and say, if I'm too systematic, am I thinking big enough to look at what's wild?
If I'm always looking for the next shiny object, am I really paying attention to the systemizing in the business? The other things like that. So this is where advisory boards and sometimes founder friends, if you do it the right way, your senior leadership team, definitely peer groups, CEO peer groups, co-founders, you know, where you go off and do the offsites.
you know, help you give you better perspective on the situation. Solo founders who don't have an advisory system in some way, and that's where I am in my business right now as a solopreneur, I have to be very deliberate in getting extra advice and different perspectives so I could see things make sure I'm not missing the obvious stuff out there. So that's the first thing.
Are you really focused on the right things to move the bar? And if you look back at this year and say, did we achieve what we want to set out to achieve this year? Did we achieve our vision? Were we mostly right? Did we make the progress we wanted to make? You know, a lot of that we could look at and say, did we really focus on the right things?
And by the way, you may have focused on the right things and things are just hard and they take a few tries. They don't always work. And that relentlessness to come back is part of it. So you might have gotten it right, but, you know, didn't make the progress you want to make. So the second, the corollary to this, are we focused on the right things, is are we really focused? And this is where...
entrepreneurs suffer. We tend to see a lot of opportunities, the shiny objects, the visions, and we tend not to prioritize and concentrate and invest and say no to the things that we're not focused on in the business here. So this is a chronic problem, of course, going from startup saying yes to everything to sorting it out and creating a more scaled up business.
is creating more focus to invest enough in the right thing. So, you know, it's a myth that if you had a lot more funding, you'd make a lot more progress. I think there's a lot of discipline in doing the right things to do them in the right way, to do them efficiently, do them in smaller steps, make smaller bets. But are you really concentrating your resources? So if you look at
What didn't work in these founders' businesses and my peer groups this year, we tried to do this, we didn't make it as far. Did you really concentrate enough effort, spend enough time, put enough tries, put enough team on it, put enough resource, get the right person on the bus? So, you know, there's probably no magic in did we do the right things and did we concentrate our effort?
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Chapter 5: How can founders ensure they have enough cushion in their business?
So what are you shifting next year? In U.S. technology, this would be called your big rocks, right? Your big projects. so forth. But, you know, a simpler version of this is we used to be like this. And we want to get to here. So this year, this period, we need to focus on this. We used to be this. Now we're this. Like a deliberate change.
that the bigger the company, the more specific you have to be about the change because people won't hear it. People go back to the old way. You know, it's just a hard muscle. So it's a new muscle. What are you doing this personally in your fitness regimen or whatever? You know, what are the new things you've got on the list for this year?
So it's not just what more things do you have on the list, but we used to be this and now we're this. That's a company changing. That's a company growing. Growth is the game here. And growth is not simple. It's not what you did before and more of it. It's every year moving things around. A $5 million business doesn't work the same way as a five-person business.
So what are the big improvements out there? What are the new layers of the cake, the new products, the new go-to-market strategies, the new departments, the new – layers of your product, what's in the roadmap. Sometimes it's just roadmap here and go to market there and that kind of steady state stuff, or at least turning the crank. But like, what are the things? Sometimes they're pivots.
Sometimes they're deliberate. Sometimes what got you here won't get you there. very typical thing as you grow. And there's few phases on the way to a 10 million revenue business that is solid and resilient and capable of a lot more growth here. So again, this is these are laws of nature. It's the human condition. And there's nothing new here that Shakespeare hasn't talked about.
You know, the hero's journey is in every movie. We start off with a situation and the hero, the founder in this case, has a problem and they're trying to get it. And it's going to be really hard. And they get some help along the way and eventually accomplish it and get transformed at the other side. Every movie, every book, everything.
Most, you know, most things we pay attention to, videos, have that kind of narrative story. We have it ourselves in our business here. And it's that change, that hard change. You know, most change isn't easy. We've grown as founders, but it's that stuff that we know we need to move forward. We know we need to give up. We know we need to stop. We know we need to build a new habit.
We know we need to put the old thinking down and create a new thinking. Any founder that goes from startup, scrappy founder, do-it-yourself, all the way to 10 million and then 50 million. And I've been pounded through that crucible as well, realizes they – They can look back at phases and through that turns if it used to be, but now we're this, there's a ratcheting of change and growth.
And it's not always as fun and magical as you would imagine, but you got to get through it. So in the universal literature or philosophy of this, there's the classic conflicts that we all learned about in seventh grade literature class, man versus nature. Man versus man, man versus himself or herself. You know, I think it can all still be defined that way.
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Chapter 6: What narrative should founders create about their business journey?
This is the stuff we don't control. This is the outside the business stuff, which, by the way, every founder has discovered that something changed outside their business, in their vertical industry, in the SaaS models, in their competition, in the economy. In the go-to-market tactics, something shifted and we have to deal with it. So that's man versus nature, all that other stuff out there.
And what has changed in the business? By the way, this is the area that it's really hardest to plan for. We didn't know. We didn't know SEO was going to be fundamentally changed as people changed. Google things in chat GPT, but so any business that was very dependent on SEO this year was really challenged by it.
So, you know, there's a bucket of things there that are challenged in the economy and our industry and our competition and so forth. So Those are going to continue to happen. Are you thinking enough about those next year to say we got some space to deal with whatever shifts are going to come at us next year?
Because they will be there and they're not really in our control, but we can respond to them. The second one, man versus man, is either the direct competition or let's call it what's happening inside our business, our internal challenges. Those are easier to see, sometimes harder to deal with. But, you know, we can look across our business and say we're good in product and everything.
and engineering and we need to innovate more and we need a new marketing strategy or right. Most companies, depending on the founder or their phase, have a great muscle. The product's great, but we need more push on the sales and marketing side. Sales and marketing is good. I need more push on the product side. It's generally one of those. But there's all kinds of growth challenges that happened.
What our tactic that got us to two million isn't really working. We got to get another tactic or two. To get us to 10 million, the size of company changed. Now we got 50 employees. What worked before doesn't work now. This is the people stuff in the business. I think I got the right team members over here on the bus and I got to manage these over here. I got to add products.
These are stuff that it's inside our company. control of the stuff we do. We don't know how it's going to work out there in the world, but we have less control of it when it leaves the building. But that's generally where planning is focused and not really talking about the game theory and how to place bets on the external stuff. We can do a lot of that internally as well.
So that's generally when you think of the plan, it's all the internal stuff that you're going to do next year. and, you know, get from here to here. We were that, now we're this. And we're going to stop this, and now we're going to start this. By the way, founders usually get pretty clear about this, and it's a surprise to their teams. You see, you've got to be very deliberate in communicating.
We used to be this, right? Okay, now we're not doing that. We're doing this. And you got to, you know, surprising how many times you got to repeat that message for people to actually hear that. So, Good news is they got the habit of this, but changing a habit is hard inside a company.
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Chapter 7: How do founders' stories shape their perspective on growth and challenges?
I got to get out of the day-to-day business. I got to hire the right people. Those are all really big challenges for founders that most people don't get through easily on their first try. Another way to look at this is I can see this at most businesses. So any business that has fewer than 25 employees is doing pretty well, or maybe they're challenged. You can look at what the company does well.
We are great at marketing and we move fast and et cetera. Those are generally the positive traits of the founder. They like doing that stuff. They're good at that. That's what we do. So business is a reflection of the founder. So here's the interesting part. The stuff that gets you stuck, that you suck at, that's difficult, that is causing problems,
That we need to fix and all of that is usually reflecting the founder, the stuff they suck at, the stuff they don't like, the stuff that every time they think about, they go, ah. And whether it's sales founders thinking about deep technology or technical founders thinking about sales or visionary founders thinking about operations, vice versa.
You know, you can look at the strengths and weaknesses of the founder and you map them pretty close to strengths and weaknesses of a business. So for the business to change. And Dave Hirsch just talked about this on the podcast here. The business to change, the founder, leader, CEO needs to see it and move themselves.
So in some sense, the business is always going to move as fast as the leadership. And the most important leader is the CEO of the business. So you may be the limiting factor, or better said, your thinking may be the limiting factor there. So that's another place to look.
is if the stuff where you're suffering in the business and struggling is a reflection of the stuff that you don't like and have suffered. There are ways to deliberately solve that. Sometimes it's move your thinking. Sometimes it's concentrate and never get the right people to solve that. And there's other ways to do that here. So what are you shifting this year? And does your team know about it?
Does your team know that you just changed the ICP to be like this? And we're no longer going after these people. We're adjusting that. Or maybe there's a bigger pivot involved. We know we tried this. It didn't work. And now we're trying this. That clarity is usually lost in communication. You know, maybe the what are we shifting this year?
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Chapter 8: What final advice does the host give to practical founders?
We know what the shifts are, but making sure everybody's clear about that. The bigger it gets, the more important the job of the CEO is to keep the main thing of the CEOs, to keep the main thing, the main thing, because people will go off in different directions and try different things. So it's really hard to concentrate effort and focus on all those important things.
and let people know that this is a betting strategy. Many of these things will work. We think we'll get most of them on the first try. We'll come back here. We have just enough information to think this is a good idea. We're all betting here. This is not, you know, many of your employees know that you're making it up and making it true because that's what you're doing.
But that's the second thing here is what are you shifting this year, really? What's your, you know, your big rocks, your priorities? This podcast is sponsored by my friends at Cypress Growth Capital. At some point in your growth, you'll know you could grow faster with some outside funding, but selling a part of your company to VCs would change your whole game.
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Go to cypressgrowthcapital.com slash practical to learn more and set up a time with Cliff Centell to see if there's a fit. Now back to our program. The third question that can help you improve the odds that you're gonna move the hard things, the big things, the important things to move your business along the path that you want.
And I didn't say what growth rate or profitability or pace, or, you know, should you have three priorities or 10 priorities? I don't, you know, it's really up to you to figure that out. You can do it your own unique way. But the third question is what help do I need to move these things and accomplish my goals.
I'm not saying that every kind of help is great and everybody ought to do everything, but bootstrap founders, especially solopreneurs, and, you know, get into new territory. It's lonely to be a founder. Some people have coaches. Some people have advisors. Some people have boards. Some people have peers. Some people hire consultants. Some, you know, sometimes help is your own team.
You know, help do I need on my team this year? Some people get help from books and content and podcasts just like this. Some people get help from ChatGPT. Very, very helpful on you. Some get help from CEO peer groups. like the practical founders, peer groups.
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