Practical Founders Peer Groups

It’s hard to create a valuable software company.

Getting the right support and guidance will get you there faster.

Now you can work on your business with a trusted group of practical founder peers who are going through the same crazy hard stuff and who can support you every month.

Each Practical Founders Peer Group is personally curated and moderated by me, Greg Head.

create a valuable software company faster

Practical Founders Peer Groups

Be part of a committed and confidential group of practical founders who are creating valuable software companies without big funding—just like you.

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

2023 enrollment is currently open. Apply now.

Be one of 15 new Practical Founders Peer Group members this year.

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 $5,000 a year—or $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:


Building Customer Traction

  • You have a working product and several paid customers using it
  • You are learning where the real market opportunity is to pursue
  • You have a small team and between $20K to $200K in annual revenue

Getting to Product-Market Fit

  • You have some traction and a small team but it’s still early
  • You are experimenting with customers, messages, pricing, features, and channels to find leverage to grow faster
  • Your team is expanding with between $100K to $1M in revenue

Scaling Your Business

  • You have a clear customer focus and your product is not changing much
  • You just need more revenues to fund your investments and build value
  • 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?

This is a great fit for you if you are:

  • 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, you speak fluent English and can meet in the morning or late afternoon times in the US.

This isn’t a good fit for you right now if:

  • Your business does not have a software product with recurring revenues. This isn’t for 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!

For Committed
Practical Founders Only

Practical Founders Peer Group membership is $5,000 a year—or $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.

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 support with Greg Head each quarter on any topic

2023 enrollment is currently open.

Be one of 15 new Practical Founder Peer Group members this year.

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

About Greg Head

As you may know, I have had a successful 30-year career starting, growing, and scaling software companies. I worked crazy 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.

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.

Practical Founders Peer Group membership is $5,000 a year—or $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.

Yes, Some minimal revenue from real paying customers is a requirement to participate in a Practical Founders Peer Group. This can be a few customers and $20K-$50K recurring product revenue to start, but some revenue and customer traction is required. 

Here’s why:

  • When you are building your product and trying to find your first paying customers, our groups can’t offer much value to you yet in how you build your particular product for your particular customer. 
  • When you are pre-revenue, I recommend you spend all your money investing in building a valuable product for the right first customer that they will pay for. You should use free online and available mentor resources to help you at this stage. 

We can still have a conversation about the eventual value to you of a Practical Founder Peer Group when you get your first customers. Feel free to sign up to have a conversation with Greg and possibly participate in a peer group as you grow. 

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. 

Each peer group meets monthly over Zoom for 3 hours at a scheduled time. Meetings with Greg are also by Zoom or phone.

We may have an onsite in-person meeting for each of the peer groups at some point each year after we get started. 

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. 

When the Practical Founders Peer Group isn’t practical for you because of time zone conflicts or urgent challenges, I also work with a few founders every quarter 1-on-1 as a strategic advisor. 

If you want to work with me as an advisor, simply fill out the Peer Group form here and let me know you’re interested in 1-1 advisory in the notes. 

I’ll follow up to discuss what you really need and how my practical advisor program might be a good fit.