Practical Founders Blog

A New Wave of 10X Better Software is Coming

A new wave of AI-powered features and products is bringing back the word "magical" to software. This has happened with every new wave of tech since the beginning of PCs and Macs. Remember how many times Steve Jobs said "magical" in his ...

The Myth of the Bigger Pie with VC Funding

The chart below says, "You should raise tons of VC funding and try to be valued over a billion $ by those private funders." This chart also can say five other things that founders should understand. 1) There is a place for VC funding. ...

Startup Luck is Important, But How Do You Define It?

Every practical SaaS founder I know works hard, takes risks, and does things normal people don’t do—for a long time. But how much of our successes came from "luck" as we define it? Most things we do don’t work out so well, but some things ...

It’s Harder to Win the LinkedIn Content Game

More people resolved to post almost daily on LinkedIn this January, as they did last year at the same time. You can see it and feel it. This means there is MUCH more content on LinkedIn, but about the same number of people to see it. AI ...

From Tech-Enabled Services to SaaS with Services

Tech-enabled services companies are a lot like a SaaS business. Many of them evolve into software-first companies with extra services. They have recurring revenues with MRR, CAC, LTV, ACV,, churn, and net revenue retention metrics. They ...

This Really Happened to Me Last Week

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 ...

Everything is a Niche of a Niche…of a Niche

Don't feel bad when someone tells you your startup serves "just a niche." It's actually a compliment. Everything is a niche of a niche...of a niche. This is an old put-down in startup-land, especially from institutional investors ...

SaaS Isn’t Dead. It’s Just Changing.

People have been sending me "SaaS is Dead" articles and posts almost every day in the last month. That makes for better clickbait headlines than the real truth that "SaaS is Changing, and It's Complicated." Here is how I see it this ...

Founder-Funding Fit is Real. Choose Wisely.

The most common conversation with a new software founder starts with the question, “What should I do about _____?” I reply, “There are several ways to do it. It depends on what kind of company you are trying to create in 5 or 10 years.” ...

Memories of My Dad on Father’s Day 2024

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 ...

Is 2024 a Bad Time to Be in the B2B SaaS Business?

SaaS company growth rates are down, SaaS app buyers are frugal, IPOs are nonexistent, public SaaS multiples are low, big tech layoffs continue, and VC funding for SaaS has plummeted. Is this the end of the SaaS era? The B2B SaaS industry has ...

The 8 Long Term Trends in SaaS that I am Betting On

I don't know what's going to happen in 2024 with SaaS funding, tech IPOs, M&A exits, or AI breakthroughs. But there are a few long-term trends I'm betting on that affect the SaaS industry. I'm not losing any sleep over what negative events ...

The SaaStock 2023 Conference in Dublin

It is great to be around so many practical SaaS founders at the SaaStock conference in Dublin this week. There was more talk of bootstrapping this year than about big VC funding. This photo is what the Bootstrap Stage looked like for two ...

The Lessons For Founders From The WeWork Debacle

WeWork announced this week that they have "a substantial doubt of continuing as a going concern." This is a pre-bankruptcy announcement. They will likely wind it down and sell off the assets to pay creditors. WeWork could have been a great, ...

Bootstrapped CEOs Can Choose to Grow Big Slowly

One of the biggest differences between bootstrapped software companies and their VC-funded peers is their time frames. Most venture funds have a 7-10 year time horizon. The companies they back need to grow fast and sell in under 10 years to win ...

Why Chik-fil-A Doesn’t Sell Hamburgers

Why doesn't Chik-fil-A sell hamburgers? Chick-fil-A is the 3rd largest fast-food restaurant chain in the US, behind McDonald’s and Starbucks. They just sell chicken sandwiches. $17 billion of them a year. Chick-fil-A doesn’t sell ...

A Bootstrapped Software Company in Silicon Valley

Bootstrapping, self-funding, and resisting big VC funding are still not very common in Silicon Valley these days. It's not as easy for startup founders to raise funding there this year, but serious outside funding has always been the main ...

Successful Software CEOs Say NO More Than YES

The most successful founders and CEOs say NO more than everyone else. How does that work? Doesn't having a bigger business allow you to say YES more often? You'd think so, but it doesn't work that way. Experienced entrepreneurs, big business ...

Why Bootstrappers Don’t Get Media Coverage

Bootstrappers are measured by their REVENUES. But VC-funded companies are measured by their VALUATIONS or their latest FUNDING. Isn't it interesting how tech and business media treat companies that didn't raise any outside funding? Valuations ...

Grow Faster By Saying No To Bad-Fit Customers

"One big reason we were successful is that we identified our ideal customer profile early, and we owned it, and then we really targeted them. "When you can start saying NO is when your trajectory starts taking off. "In the beginning, you’re ...

Scaling Customer Support For SaaS Companies

How are fast-growing SaaS companies scaling up the human-powered customer success and customer support that can't be automated? The tech talent crunch is real in every country around the world. In this month's Ask an Expert in-depth video ...

When Not Getting Big VC Funding is the Best Thing

I hear from founders every week who pitched big investors and were turned down with responses like these: “Your market is too small” “We don’t like services revenue in the mix with SaaS” “We don’t like transactional revenue" These are ...

Startup Luck Is Usually Overestimated At First

The role that good luck plays in startup success is usually overestimated by founders as they are building… and underestimated after they have achieved some success. I wrote that as a short post on LinkedIn here. Then my friend Hamid ...

The 20 Most Common Types Of Software Companies

Here are 20 of the most common types of software companies that I see right now. Which one describes your company? 1) The startup just starting. More hope than traction so far. 2) The big public company grinding it out every quarter. 3) The ...

Announcing the Practical Founders Podcast

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 ...

Use The Unsuck Playbook When You Get Stuck

The highest-leverage way to grow a business faster is to DOUBLE DOWN on a target market, sales channel, use case, or marketing message that is already working very well. But there's another playbook that also gets companies (and careers) ...

Mentors And Advisors Have a Powerful Magic Trick

Every mentor, advisor, consultant, board member, or peer founder has a powerful magic trick when they give feedback or advice to an entrepreneur. They are not you. They haven't been fanatically thinking about your business all day and all ...

Entrepreneurs Are Both Optimistic And Realistic

Entrepreneurs are optimistic. They find hard problems and think "I could fix that." Normal people don't do this. Most people run into problems or frustrations and just think "that sucks." A big part of any entrepreneurial opportunity is the ...

Crazy Entrepreneurs Create Our New Future

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 ...

Co-Founder Problems Can Kill Your Startup

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 ...

Use The 10% Rule To Spend Less And Grow Faster

One of the most useful tools I use in entrepreneurship and marketing is The 10% Rule. I use it every day. It works like magic well when looking at any market or any set of execution results. It's like the 80/20 Rule of the Pareto Principle, ...

What Kind Of Funding Are You Actually Raising?

I talked to 10 startup founders last week who are raising money from investors, have raised, or are planning to raise. I always ask this question: What kind of money are you raising? This is where the fun begins in our discussion. Most ...

Be Prepared For A Little Luck

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 ...

Startups Are Experiments. Keep Trying.

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 ...

When Should A Founder Go Big And Bet It All?

I caught up with a founder friend yesterday to hear about his new Web3 startup that uses blockchain, cryptocurrency, and NFT technologies. We last spoke when we both lived in Phoenix a few years ago. Now I'm in Dallas and he's somewhere ...

This SaaS Company Grew Faster By Saying No

A founder I advise just sent their annual 2021 investor report today. They grew from $1.8M ARR to almost $5M ARR this year. This means the value of the company more than doubled too. I'm a happy investor in this software company. They are ...

TAM Is A Sham For Practical Founders

"How big is your potential market?" is an interesting question. But it's not very helpful to software startup founders. Here's what's actually useful: "What's the fastest way to get 100 or 1000 extremely happy customers who pay you and ...

Where Are All The Finish-Ups?

Startups are everywhere. Everyone seems to be starting something. Where are all the finish-ups? Where are all the founders and their teams getting to their end game? For all the starts who raise money from investors, finishing up is ...

Startup Ideas Are Not Up-And-Running Businesses Yet

Two weeks ago I volunteered to judge a live startup pitch day with 23 undergraduate presenters at a major university in the Dallas area. Seven of the 23 startup pitches were already micro-businesses run by these students (or were very close ...

Gregslist Phoenix Is 5 Years Old This Week

Gregslist Phoenix is 5 years old this week. Gregslist.com/Phoenix I published my first curated Gregslist of 126 Phoenix software companies in August 2016. Back then, tech leaders and SaaS founders in Phoenix didn't think there was much going ...

AZ Software Podcast Interview With Greg Head

Last week in Phoenix I spent an hour with my good friend Hamid Shojaee to talk shop on his AZ Tech Podcast. Here's what we talked about: - What's happening in the Arizona startup tech scene right now - Which Phoenix software companies are ...

Grow A Startup Out of Your Existing Business

There is a lot more startup innovation funded by existing businesses than anyone sees. It just doesn't make the headlines that big funding does. Most of the founders I work with are managing their products and services as a portfolio. It's a ...

The Texas Software Industry is Growing Faster

There are more than 1700 software and SaaS companies in Texas in Austin, Dallas, and Houston. There were already a lot of software companies in Texas before 2020 when more tech companies moved here. 742 software companies on Gregslist ...

All Startups Need To Play A Category Game

"Why do we need to worry about our category as a startup right now?" That's a common question. The category game is not for every business. Small businesses play in existing categories. Big businesses dominate categories that are already ...

The Myth of Scaling With A Wide Net

I have been looking for an example of a successful company that started "wide" by being many things to many people and then grew from there without focusing. I have been looking for 20 years. I still haven't found one. It's totally ...

Which Of The 3 Category Games Are You Playing?

Every buyer categorizes everything they buy, including your product or service. Every company is playing one of only three category games. The first rule of the game is to know which game you are playing, but most startups and growth ...

How Is Marketing Different Than Sales?

A salesperson selling face to face can find a customer problem and then select one of their many solutions to solve that problem. That's how sales works: "We can fix your specific problem from our menu of solutions." That's not how marketing ...

Founders are Chief Believer Officers

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 ...

Find The Right Funding For Your SaaS Startup

When savvy founders with real businesses ask me if they should raise money from investors, my first response is always the same: “Don’t raise money right now. Wait a little longer and gut it out.” I know they desperately need additional cash to ...

Keep Moving Forward and Don’t Stop

Last year I met with over 300 founders and CEOs, worked deeply inside 30 businesses all over the U.S., and spoke to thousands of people at conferences and events. Despite that, my own business wasn’t a cakewalk and many things didn’t work out ...

Why Chick-Fil-A Doesn’t Sell Hamburgers

Chick-fil-A is now the 3rd largest fast-food restaurant chain in the country, behind McDonald's and Starbucks. They just sell chicken sandwiches. $13 billion of them a year. Chick-fil-A doesn’t sell hamburgers. Their average revenue ...

The Biggest Myth About Marketing

All of us experience marketing all day long, almost everywhere we look. Surprisingly, this causes most people think they understand the marketing game. That’s like eating a nice meal at a restaurant and proclaiming you can cook it yourself ...

Hard Lines Create Long Lines

When I see a movie or a painting, I see the result of what someone created. I don’t think much about how it was made. I don’t understand it like someone who studied art or made a movie. When I see a website, ad, sales pitch or product ...

Entrepreneurs Figure It Out

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 ...

How I Got Great PR Results On The Second Try

Public Relations is one of the trickier parts of the marketing game. It’s not like digital advertising or email marketing, where you can push a button and make measurable things happen right away. A year ago, I hired a savvy PR agency to ...

Beware the Startup ADD Trap

Discovering and executing on your Scaling Point is a necessary requirement for growing a little company into a big one. But why is it so rare? There are two reasons why Startup ADD is an almost universal disease that is very hard to ...

Sorry, Not All Startups Should Be Funded

Surprised at how hard it is to raise funds for your startup or growing business? Almost every entrepreneur I know who has tried to raise money is surprised by the incredible amount of time, effort and energy needed to raise equity ...

Your Business Is Defined By What You Say No To

Your audience doesn’t always hear you as clearly as you think they do. What your business is and why it exists may be clear in your head, but most entrepreneurs are surprised when they ask their prospects, customers and even their own ...

Three Brothers and Their Billion-Dollar Businesses

Last Friday I had the opportunity to interview three entrepreneurs who have created billion dollar companies at the Venture Madness investor event in Phoenix: Justin Kan, Steve Huffman and Daniel Kan. Justin, Steve and Daniel have each ...

27 Awesome SaaS Metrics Resources

The software industry has almost finished its 10-year conversion to SaaS (software as a service). It's software that runs on PCs, web browsers and mobile devices, and is centrally hosted on servers outside our data centers (in “the ...

The Thing is Never Just the Thing

The product your customers evaluate, purchase, use and talk about is not just the product you deliver to them. The actual product is critically important, but it’s not the “whole product” in the eyes of your customer. There’s more to the story, ...

The Phoenix Startup Scene is Booming

I have been part of the Phoenix startup and software scene for 20 years. I see ten times more activity in startups and fast-growth software companies in Phoenix than there was just five years ago. As an executive leader, I have helped two ...

Startup Founders Need to Say No More Often

Creating a new venture and surviving the brutal startup phase often feels like a negotiation in which you need to say Yes to everyone just to survive. This is the fastest way to end up in startup purgatory – you get started but you get stuck on ...

Greg Head’s Next Exciting Adventure

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 ...

The Freak Show is Never in the Main Tent

Even though I am 46 years old and live 1500 miles away from my Dad, not a week goes by when I don’t hear his voice in my head telling one of his many stories about business, marketing or management. We still talk weekly, but I am most often ...

Every CEO Needs to Know Digital Marketing Basics

Remember the old days when marketing resulted in printed material you could touch and feel? Just 10 years ago, the majority of marketing artifacts included printed brochures, product packaging, magazine advertisements and direct mail letters. ...

Rule #1 – Make a Great Freaking Product

Imagine a world where people don’t listen to what your business says about your new product: they only listen to what other people say. A world where there are hundreds (or thousands) of choices for almost every product. Where every buyer ...

The Target Market Trap

Ambitious entrepreneurs naturally aim to create large companies in large markets. They make their plans, build their newfangled products, assemble scrappy teams and then set out on their holy quests to be big winners. But most startups don’t ...

The Basic Elements of the Angel Investor Pitch

Angel investors regularly hear pitches from local entrepreneurs who need money for their growing startups. Unfortunately, too many entrepreneurs don't succeed in their first meeting with potential investors. How can you be more successful ...

CEO Selling Doesn’t Scale

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 ...

Improve Your Website Using Google Analytics

Do you know what visitors are doing on your website each week? Where did these visitors come from? Which pages did they think were most important? Which search terms brought them to you? Using Google Analytics, the popular and free website ...

Be a Fanatic to Scale Your Service Business

Where do CEOs of small service companies struggle most when trying to create a "scalable" service business that can grow to be a large company? They underestimate the amount of refinement and development of their service offerings, marketing ...

Is Your Focus Narrow Enough?

You've been working hard to build your new product or launch your service. You're excited because your first potential customers are still interested in buying from you, despite several delays. Now it's time to start chasing more customers by ...

The Two Most Important Questions

Think about it: Who is your customer? What does this customer value? These are two of Peter Drucker’s “Five Most Important Questions” for your organization. I often find myself returning to Drucker's questions in strategic discussions about ...

The Marketing Trap

Successful startup entrepreneurs almost always have impressive skills in two areas: product creation and sales. They find problems in the marketplace and create products or services that satisfy those needs with teams that can deliver the ...

Outliers by Malcolm Gladwell – Book Summary

Outliers is the latest book from best-selling author Malcolm Gladwell. He also wrote The Tipping Point, one of my favorite marketing books. Gladwell is an astute social researcher and a master storyteller. His other books and his columns in The ...

Marketing Communications is Getting Harder

The marketing communications challenge is getting harder, not easier. Why? Because there are more communications channels than ever. Each channel you use requires time, effort and some expense. And it’s not easy to be proficient with so many ...

Working with Informal Advisors and Mentors

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 ...

Create Websites Using CMS Platforms

It used to take considerable expense to create a high-quality company Website, even for small businesses. I just finished a project that confirms that popular and inexpensive Website creation tools are taking much of the development cost and ...

Simplify the Message

One of the hardest things for entrepreneurs to tackle is the definition of their core business "positioning." Positioning is known by many names - your focus, your marketing strategy, your elevator pitch, your business description. This ...