Practical Founders Blog

I had a great time visiting three great SaaS founders in London last week. Simon Berry, Wayne Cartmel, and Scott Rowlandson are three UK SaaS CEOs in my Practical Founders Peer Groups. In-person time still matters, even when you talk ...

Thousands of bootstrapped SaaS founders have built valuable software companies that created serious wealth for the founders. But few of these entrepreneurs started with the only goal of making that much money. It's an entrepreneurial ...

Even highly successful software companies with huge exits struggle at every growth phase, experiencing near-death experiences similar to those that didn't grow bigger. They just found a way to keep going and growing. Brian Hamilton is one ...

As companies grow, the role of the entrepreneur changes from scrappy founder to CEO of a much bigger team. It's a different game that all founders can learn to play, if they want to take on the new responsibilities. The impact of your ...

I helped a stranger with directions on the slopes in Park City yesterday when he said, "Wait, do you have a podcast? I recognize your voice." It turns out it was Jeremy Clarke, one of the amazing SaaS founders I have interviewed on my ...

If you still love working in and on your business every day, would you sell it when it grows and becomes more valuable? Why not "Build and Hold?" Most practical SaaS founders love what they do, despite the long hours and the hard ...

Last week, I hosted 25 SaaS CEOs at our first Practical Founders Summit, which lasted two days in Phoenix. It was awesome to meet in person with Practical Founders Peer Groups members after meeting monthly on Zoom to work on their businesses ...

Practical SaaS founders who defy conventional startup wisdom usually win bigger with much better odds. They do the opposite of what their startup ecosystem echo chamber of investors, experts, and peers tells them: there’s only one way to do ...

About half of the 40 SaaS founders I work with have shared that they are getting tired and can't shake their grumpy moods as quickly. Is this a mid-summer dip or something deeper going on? Here are the top reasons I hear that founders are ...

Being the CEO of a growing SaaS company can be lonely, even with 15 or 50 employees. This is especially true when the company is bootstrapped or lightly funded without big VC funding. VC funding comes with board members, big lawyers, ...

Here are a few memories of my Dad on Father's Day. Jim Head was a lanky kid from Dearborn, Michigan. He grew up to serve as a Navy pilot for a few years and eventually became an advertising agency executive in Chicago. He had ambitions, but ...

“Our SaaS product works, we have happy customers, and we have enough leads—but our demo close rate is too low.” Every day, B2B SaaS founders tell me about the hard problems they are working on in their startups. A low close rate is one of ...

It can be overwhelming for SaaS founders to deal with so many different and complicated things every day. Some entrepreneurs run out of energy and get stuck on their startup journeys. And the mental list of questions, tasks, and goals expands ...

Entrepreneurs tend to be generalists, but our talents and interests are not evenly distributed. We channel our superpowers to power our early startup progress. Most times, we are unusually good at a few things. We hate to do other things ...

This SaaS founder bootstrapped his first company and did pretty well when he sold it, but he didn’t want to go back to stressful 80-hour weeks again. So when he started his second SaaS company he decided to work reasonable hours to spend time ...

Corporate refugees can make great entrepreneurs, especially when they were the frustrated doers who didn't fit the corporate mold. They are the ones who ask too many questions, break the rules, tell harsh truths, and frustrate their bosses and ...

I talk to 500+ software founders and CEOs a year all over the world. I'm amazed that every entrepreneur's story is different.  Different founder personalities and backgrounds  Different times and tech cycles  Different markets and ...

Startups are glamorized. They can look pretty cool from the outside. This is not helpful to serious new founders. Sure, there are occasional breakthroughs and flashes of good fortune. But mostly it’s grinding away. Trying again. Fighting the ...

It's lonely being a software startup founder. Even when you have a leadership team and 15 or 50 employees.  Your family and neighbors don't have a clue what you really do. You can't talk about your really hard issues or deeper questions ...

How much of your health, your family and marriage, or your sanity would you sacrifice for the chance to win big with your crazy startup? Practical founder Lloyed Lobo describes this Silicon Valley all-in addiction as “unicorn porn"--Why aren’t ...

So you have an idea for a software product and you're thinking of starting a company to build it. I talk to hundreds of these folks a year, year after year. Here are 3 things that can help you increase your odds of success when you get ...

How many founder stories have you heard about grinding hard for a long time and then finally selling their company to “win a big prize?” But choosing your business OR your life is just one way to do it. Practical SaaS founders have another ...

Most founders who sell their companies eventually start another company or create a new project. Old habits die hard for most former founders. But there’s also a type of software company founder who intentionally built a valuable software ...

Successful software entrepreneurs are just abnormal people who do abnormal things. That’s not better or worse than anyone else. We just do things that “normal” people don’t do. That’s usually where the opportunity is. If everyone is doing it or ...

Every time I talk to a successful practical SaaS founder I hear about a different way to start, build, and scale a modern software company. Unlike the VC "Get Big Fast" startup game, there’s no template you have to follow when you bootstrap or ...

In the last three weeks, I talked to 56 practical SaaS founders from all over the world about their products, businesses, and their visions. Since they aren't trying to raise outside funding to grow their valuable software companies, they all ...

There was a hidden secret in the rooms of two startup funding events I attended last week in Phoenix. The richest people in the rooms of both events were the founders who had built and sold valuable software companies without any outside ...

Practical founders often tell me something that they don't talk about much: It's lonely being a software startup founder. Your family and neighbors don't have a clue what you really do. You can't talk about your really hard issues or ...

Most founders who sell their software companies don’t join the leadership teams of their acquirers. Or they don’t stay around any longer than they have to. But what if you sold your beloved business to a bigger company that had the same ...

I hosted a dinner with 15 founders last night at the SaaSOpen conference in New York. After an hour of great conversation, I realized I was talking with founders from Poland, France, India, and Tel Aviv at my table. Other tables included ...

Many new entrepreneurs hesitate to ask for help from experienced founders and savvy mentors. They are missing out on POWERFUL INSIGHTS that can help them overcome their big challenges or learn how to approach something new. I have had over ...

I interview successful SaaS founders every week on the Practical Founders Podcast. Every founder story includes the savvy bets by the founders, the extreme hard work for long years, and the balance of risk-taking and good timing. I asked them ...

February is here and it's reality time for our 2023 New Year's personal resolutions and the quarterly plans and goals in our businesses. I make personal and business plans, but I don't accomplish everything I set out to every month or every ...

The best founders I know get the best advice from experienced entrepreneurs and other experts. Great advice is usually the result of the founder's investment of time in their network of experts and experienced entrepreneurs who want to ...

I talked with a young startup founder who was more than a little panicked by the sour financial news in tech recently. Venture investment is down by almost 50% this year. New unicorns are rare again. Tech layoffs continue. Crypto crashed. Hot ...

It takes confidence to start and grow a company. It also takes a healthy dose of humility. It's strange how experienced founders can do both at the same time. Confidence helps you keep moving forward when it's hard. And persuade customers and ...

What if your first startup didn’t go anywhere and it ate your life savings? Would you do it again? If you are like Brad Redding, you’d start another software company five years later to prove you actually learned some useful lessons ...

Twenty years ago, entrepreneurs used different words to describe what we now call mental health challenges. Stress, depression, anxiety, burnout, and nervous breakdown were the words we used back then. We didn't talk about it much. But it ...

Here's how I think founders, entrepreneurs, and CEOs should take any business advice, including any advice from me: Consider everything you hear as an interesting POSSIBILITY to consider, including that which sounds like a ...

The startup game for investors is pretty much about this: "What do we know and what do we not know yet about this founder, their team, their product, the business model, and the market?" This is why early traction with paying customers, ...

Two years ago I started a new habit during the COVID lockdown that I haven't stopped. It has made a huge difference in my business and in my life. The COVID lockdowns are behind us, for now, but this habit keeps going. It's this: I ...

When a startup founder creates a software company that another company acquires, they become members of an elite club: founders who have sold their companies. Here are a few reasons second-time founders get more attention and credit than ...

What if you saw an obvious problem in the world that you could solve with a new software product? And you and your co-founder friends quit your jobs to live off your savings to build a product you could sell... And then it took two years ...

Multiple practical founders this week have shared something with me that they don't talk about a lot. It's lonely being a software startup founder. Your family and neighbors don't have a clue what you really do. You can't talk about ...

I'm excited to announce my newest project--it's live today! The Practical Founders Podcast has in-depth interviews of serious founders who have built valuable software companies--without big funding. There are MANY practical founders who ...

When my son graduated in 2017 with a degree in electrical engineering, he didn't join a big company for his first job. He created a tech startup with a friend. For the next few months, his friends and his parent’s friends offered ...

Show me something that is changing in our world… And I’ll show you a crazy person behind it all. Crowds don’t change on their own. There’s always a “crazy” person and their team that started the wave. People tell them they are crazy ...

I talked to a startup founder this week whose business is growing steadily. But he has issues with a cofounder. It's killing his hope for the future of the business. Cofounder problems are one of the challenging issues that can prevent a ...

I didn't think about my own luck when I was in the midst of my career. Most things didn't go my way and I worked almost all the time. Where was the luck in that? I hoped that working hard and being savvy would create more ...

The people who succeed are the ones who say no to the things that don’t help them succeed.

A startup founder I talked to this afternoon was in a bit of a panic. "Is it going fast enough? Should we be doing different things?" So I asked her what she had learned since the last time we talked a few months ago. She rattled off ...

In the startup world, there is a lot of conversation about raising VC funding and successful exits. But what if you didn't do either in your software business? I know thousands of software company founders and CEOs. By far the happiest ...

For 30 years I have been an avid student and practitioner of time management systems, planning approaches, productivity software, and mental approaches. It's mostly to help me manage my procrastination and distraction tendencies, which I fight ...

I have this conversation 10 times a week: Me: How’s it going over there? Software startup founder: Great! Me: How’s it really going? (pause) Founder: We’re f*cked. It’s all hard. Me: Welcome to the club. That’s why everyone ...

I talk to hundreds of SaaS startup founders and software CEOs every year through mentoring, networking, speaking, advising, consulting, investing, events, and now the Dallas Software Podcast. I'm amazed that every story is different. ...

How long will it take to get to your next big startup goal? Here's my rule of thumb when estimating how long a venture or project will take to make real progress. Double it. For extra measure, work even harder, add more people, and run ...

When you start a company, you do every job in the business. As you add employees, you stop doing a few things yourself and hire others to do them. For companies that grow big enough, your team members eventually do all of the day-to-day ...

I’ve noticed something that all successful entrepreneurs say when they are interviewed about how they grew their crazy startups into big businesses. You also hear it in interviews with Olympic gold medal athletes. And when successful ...

At a recent event for Phoenix tech leaders, fellow entrepreneur Adam Toren and I were catching up over beers. Adam waved to a friend across the room. Gabe walked over to join us. “Hey Gabe. How’s it going?” Adam asked. “Great!” Gabe said ...

After almost five years, Friday, October 30, 2015 was my last day at Infusionsoft. It has been an honor to be part of several exciting phases of growth at Infusionsoft and to accomplish world-changing contribution with so many passionate and ...

What’s the biggest difference I see between a $1 million technology company and a $10 million technology company? You might think it's something like the quality of their products or the size of their management team, but it's not. The key ...

Many entrepreneurs and CEOs ask me if they should create a formal Board of Advisors so they can get advice from experienced leaders or well-known figures in their industries. The most common reason to create a formal advisory board is to ...