Practical Founders

It’s lonely being a software startup founder.

What if you could rely on a trusted group of founders who were going through the same crazy hard stuff and who could advise and support you every month?

What if these high-impact groups of practical founders were curated and organized by Greg Head?

Starting Now

Practical Founders Peer Groups

I am currently running three Practical Founders Peer Groups with savvy SaaS founders from all over the world. 

Every month we will help you make progress in these three areas:

  1. Drastically improve decision-making in the crucial areas where you are struggling.
  2. Learn and share deep insights on how to grow your B2B software company most effectively.
  3. Get the emotional support you need to stay sane on your crazy startup journey.

I am confident that every member will experience million dollar+ impact in their business. 

Apply now to have a brief conversation with Greg Head to see if it’s a good fit for both of us right now.

Join a Practical Founders Peer Group

A Practical Founders Peer Group is a committed and confidential group of 6-8 founders/CEOs who are creating valuable software companies without big funding.

Each peer group cohort meets monthly over Zoom for 3 hours at a scheduled time. The monthly Practical Founders Peer Group is a fast-paced and structured business meeting that I moderate to help you get savvy perspective and feedback on your biggest challenges.

You’ll also get regular 1-1 access to me, Greg Head, as you grow your business and face new challenges. 

“Having a trusted group of other savvy SaaS CEOs with whom I can discuss my ideas and challenges every month has made all the difference for me. And Greg’s guidance, ideas, and network have been worth their weight in gold!”

— Dave Lee, co-founder and CEO, PlusThis

The Practical Founders Peer Group is $1,500 per quarter with an annual commitment.

This isn’t a casual meetup of founder friends or another optional meeting where you can multitask and do other things. And it’s not a workshop with a structured step-by-step curriculum.

This is a structured monthly meeting with a trusted group of savvy founders who are also building software companies at the same stage of growth as you.

All Practical Founders Peer Groups have serious, committed founders with diverse backgrounds, but I organize each cohort group around their current phase of growth to focus on the unique challenges of each phase.

Practical Founders Peer Groups based on your growth stage:


Group One: Just Getting Started

  • You have an early product to sell and are getting your first customers 
  • You are learning where the real market opportunity is to pursue
  • You have a small team with $20K to $200K annual revenues

Group Two: Getting to Product-Market Fit

  • You are still making major changes in the product and strategy
  • You are experimenting with customers, messages, pricing, features, and channels
  • Your team is expanding with between $100K to $1M revenues

Group Three: Scaling Your Revenues

  • You have a clear customer focus and your product is not changing much
  • You just need more revenues to fund your investments
  • You plan to sell at some point when you are much bigger
  • Typically over $1 million in revenue

Ideal Candidates

Are You a Good Fit Right Now?

19 practical founders are currently participating in three active Practical Founders Peer Groups. 4 open slots are available right now. 

Ideal candidates should be:

  • A practical founder who is creating a B2B software company without big funding. Either bootstrapped (self-funded in some way) or lightly funded (angel, one-and-done seed) while heading towards sustainably funding your growth with revenues.
  • Able to fund your venture without significant outside funding for at least 12 months.
  • Anywhere in the world, but you speak fluent English and be able to meet in the morning or late afternoon times in the US.

For Committed
Practical Founders Only

The Practical Founders Peer Group is $1,500 per quarter with an annual commitment.

Peer groups require equally high commitment from all members. These powerful relationships don’t just develop in one or two meetings. It gets better and more valuable each month.

I am making a serious monthly commitment and expect the same of each peer group member.

Every member of each group makes a serious commitment to themselves and their peers by showing up every month at the scheduled time, unless there is a dire emergency.

Also included with your annual commitment:

  • Expert Zoom interviews to ask an experienced practical founder any questions in a private members-only session
  • Private Slack group to ask questions and share resources with your peers
  • Access to peer practical founders or expert mentors who have the specific experience you need
  • 1-1 advisory session with Greg Head for 1 hour each quarter on any topic

I’m as committed to these Practical Founders Peer Groups as you are to your startup. 

Let’s have a conversation to see if it’s a mutual fit for both of us to make this commitment together. 

About Greg Head

As you may know, I had a successful 30-year career starting, growing, and scaling software companies. I worked hard with amazing people. I had some big successes and countless opportunities to learn along the way.

Now I help serious software company founders all over the world almost every day via Zoom, phone, and my popular LinkedIn discussions. I am an active mentor, advisor, investor, and tech community instigator.

I have also created and run several SaaS CEO peer groups both in person and on Zoom. Leading high-impact peer groups with serious SaaS founders is one of my favorite things to do.

Peer Groups FAQs

Just fill in the simple application form with basic information about your company and your situation. Greg Head will follow up with you directly to answer any questions you have and make sure it’s a perfect fit for you right now.

These three Practical Founders Peer Groups will fill up quickly. Since it’s just me leading these groups, there is limited availability. I will start a waitlist for practical founders who want to join one of these groups in the future. 

We will likely have an in-person 2-day event for each of the peer groups at some point after we get started. Most founders who are interested in these groups have expressed strong interest in spending time with their peer group members for a 2-day offsite event with business and social activities. 

Membership in a Practical Founders Peer Group requires an annual commitment and at least 75% attendance in our monthly 3-hour peer group meetings. 

These groups will continue for years. Some members will move to a different group level as they grow, new members will be added, and some founders will sell their companies and “graduate.”

Several peer groups I have previously led kept going every month for over 5 years.

The Practical Founders Peer Groups wouldn’t be a good fit for you right now if:

  • Your business does not have a software product with recurring revenues. This isn’t for tech services businesses, B2C software companies, consultants, or web3 companies.
  • You’re not the CEO. This isn’t for non-CEO co-founders or C-level or VP-level leaders.
  • You can’t fund your operations without outside funding for the next 12 months. If you are running out of money and can’t afford a cash investment, I don’t want to take your last dollars in the bank!
  • You want to talk about raising money, pitch decks, investor networking, or pitch contests. We’re not going to be wasting any time on raising money and pitching investors!

A CEO peer group is an organized group of CEOs who meet monthly in a confidential setting to work through their business challenges and share insights. In a trusted and confidential environment, it becomes a powerful forum to discuss your most difficult challenges and get alternative perspectives. These peer CEO relationships usually become deep and lasting. CEO peer groups are not new. There are CEO peer groups in every major city which include CEOs and owners of companies of similar sizes across industries, typically between $5-$50 million in revenues. Some groups are facilitated by a coach and others are self-moderated.

There are popular peer group organizations for CEOs and business owners that have local chapters in most cities around the world, including the Entrepreneurs Organization (EO), Vistage, and Young Presidents Organization (YPO). Each requires significant financial and time investment with local, in-person, full-day meetings every month for their groups. Most members have businesses in other industries like manufacturing, healthcare, services, or distribution.

Unlike these groups, Practical Founders Peer Groups are just for founders of startup and early-stage B2B software companies. We focus exclusively on the serious issues facing practical founders who are growing valuable software and SaaS companies without big outside funding.