How Jeff Twiddy Built a 3000 Member Site With Free Trials And Annual Upsells

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Jeff Twiddy is one of my very own students from the Flip Your Life Community. Jeff is a former school teacher and football coach that started his own membership site in the education space a few years ago.

He has now built an incredible membership site with more than 3,000 members paying an average of $47/month. His resources are used in hundreds of schools all over the world.

In today’s episode we go deep into Jeff’s membership site and discuss how to up-sell free trials into annual members on your ‘Thank You’ page, the life-changing nature of creating your own monthly recurring revenue business, and how outsourcing content creation allowed Jeff to focus on building his million dollar membership.


What You’ll Learn:

  • You can’t skip levels of success. (5:40)
  • Your friend groups have to change as you progress. (11:15)
  • Big things happen from small things. (18:00)
  • The reason you should sell one thing. (38:07)
  • How to find your point of least resistance. (43:00)
  • How to stay ahead of your members. (48:00)
  • Why vision and your art is everything. (55:00)
  • Everyone getting to be as selfish as possible is the goal. (1:00:00)
  • The best ways to slow down churn. (1:07:00)
  • Don’t spend more money than you’re making! (1:25:00)
  • What positions should you hire first? (1:35:00)


Show Notes

You can’t skip levels of success.

We hav an analogy in the Flip Your Life Community that is basically a 4-stage infinity circle of what entrepreneurs go through. You have to cycle through it to get to the next level.

  1. You have to yearn for something.
  2. You’ve got to learn about it.
  3. Grind and earn it.
  4. You can burn it up.

You just keep going through these cycles as you keep going to the next level.

I think back to horrific things that I had to do an intern. Like one time there was 5 years of tape and I had to watch every single one of them and label them. It probably took me two weeks just to get them on shelves before I could even watch them.

Like Jeff said, in the beginning you will have transitions and not and not even realize they’re happening. You go from just trying to figure everything out to having everything figured out and go to the next level.


Your friend groups have to change as you progress.

You need somebody like a coach to push each other every day. You have to find those people that will push you to the next level. People that have been to the next level or know what the next level is.

Disclaimer: these people may not be your permanent group. Actually, they never are.

The group my wife Jocelyn and I were in changed dramatically when we quit our 9 to 5 jobs. It’s changed two or three times since then too!

You have to surround yourself with the right people! 

For Jeff and I it’s just like us coaching in the weight room. There was a kid at the last school I was at before I quit. I had like ten quit racks. So I based the entire workouts on those squat racks. We would always max at about 8 weeks, give kids time to grow. We would always group 4 people together by the people who were closest inter own weights. Theres’s two reasons for that 1) it was efficient - we were not changing as many weights,2) those 4 kids are constantly competing against each other to help each other grow. And, they did! Those groups were changing every 8 weeks! What happened was the smallest guy in each group was chasing the biggest guy. Some of the reason the smallest guy was the smallest is because of the amount of time he was putting in.

This is true in memberships too! Even my higher level 1-on-1 clients feel at times that they are just not making the progress they want. My #1 question is always: “how many hours did you put in last week?”

If your goal is to grow you’ve got to either roll up your sleeves or open your wallet.


Big things happen from small things.

I specifically remember getting two messages form Jeff Twiddy.

  1. The first explained who Jeff was and that he had been listening to the Flipped Lifestyle Podcast. He had launched a membership site and made money! Jeff just followed what we were saying on the podcast for several weeks and made money - without even taking the courses yet!
  2. He messaged telling me that he began making enough money that he could quit his 9 to 5 teaching and football coaching jobs!

My wife Jocelyn and I are known as membership experts that help people quit their jobs and make massive success if they want. It’s so funny when people find that branch how everybody’s business evolves totally differently from that point on.

We have multiple businesses ourselves but we spend 99% of our time on the brands of the Flipped Lifestyle and Membership Masters. That’w what our focus is on and that’s our path.

Jeff did things a little differently! Jeff started his membership with just focusing on teaching Geometry because that’s what he was teaching in school. He personally created the full curriculum for his first Geometry course. He created the website, the course, everything with nobody helping!

Then, Jeff hired a teacher that he worked with in the same school building to start Algebra I and II, Pre-calculus, Pre-Algebra, and the rest of his courses. They all were kept separate with separate blogs, activities, and everything. They were completely different funnels, shopping carts, the whole kit at caboodle at first. At the time he didn’t have the money to pay someone to do it all together and at once.

The reason that Jeff’s blog were so successful later on was because Jeff took the things that teachers struggled with the most and gave them the solution. He gave them how to teach the lesson and make it soundalike a real-world thing because the first thing kids ask is, “when am I going to use this again in my life?” So, for every lesson from each unit he wrote a blog about it and gave them the real-world connection. He gave them a play-by-play of how to create the lesson to the kids so they can learn it. Then, he sold them the resources to do it on a grand scale.

Jeff has now transitioned everything together in the same membership site! Going back he wishes he would have taken all those different course blogs and moving it all to the same blog under sections. His SEO would have been much better, gotten more views, which meant he would have gotten better rankings.

Jeff’s grander scale is to get every teacher on earth, in every grade, to be using his products in 5 to 10 years!

The takeaway? Invest in yourself and move forward!


The reason you should sell one thing.

Most math teachers teach more than one thing that’s why Jeff wanted to put them all in one place together through his online membership!

Now not only can they all communicate and help one another, they can spread Jeff’s message and his site!

I’m a huge believer that you only need to see one thing!

Ex. There was a debate on the domain name for Membership Masters. There was a debate whether this podcast would be its’ own thing. But it’s not, it’s just going to be a part of Flipped Lifestyle. The membership for Membership Masters will be by itself, there will be a category for membership masters, a playlist for Membership Masters. It’s just overall branding, it’s just in one place. We want to sell you one thing and then the next things which is usually a renewal!

Jeff now has 8 different blog total - talk about prolific! So that means before he consolidated he was running like 8 separate businesses. It was absolutely consuming him and understandably so! That is why now everything is set categorically and funnels not the same place.

Jeff’s long-term goal is to now put his science-based business and math-based business together all in one place!

It’s like Wal-Mart: everything that everybody needs is all in that one building, right? But when you see a commercial for Wal-Mart it’s like, “Pepsi’s on sale for $2.99,” you’re pulling in all the soda drinkers.

As it stands now, Jeff has a great example of of this! One of Jeff’s funnels that he has for all of his math sites. Let’s say someone comes in through one of the Geometry lessons. They decide to join the membership. As soon as they buy it says, “hey, do you also want to add this (other math course) too?’ and it adds a monthly recurring of those additional added courses. This way, he ultimately gets them in at the amount he wants. In general most people are paying the exact same amount!


How to find your point of least resistance.

What I’ve learned from coaching so many people over the years is that there is a point of least resistance for every niche that you can find. It may not be a dollar trial.

I’ve got one person that has membership that she has at like $297/month. Her point of least resistance is $97/month - it works better than free trials! There is such a gap between the high-price monthly payment so that people understand that you can’t get it for free. Her space has a number of higher economic status people in it and so it wouldn’t make sense to offer a free trial.

It would be like me offering $500/month for something and offering the first month free. That doesn’t make any sense. You’ve got to be careful not to de-value the monthly offer with your trials.

I’ve found that dollar trials work great under $100. at that price-point throwing in a free trail at that point is only going to boost your numbers.

If you’re charging $49/month your point of least resistance might be $29/month. Then you take that money and every first payment you put into ads and then you go get more trials. By doing that you just create money machine!

Don’t do a trial when you first launch your membership! They will come and go and never come back. You have to create culture in first 50-100 members and you can’t do that with trial members. 40% are tire kickers and need people with commitment!

My thought process is usually: whatever you want to charge let your beta members come in at 25% of that. It keeps the tire-kickers out and creates a significant discount to where the value is there.


You have to stay ahead of your members.

Giving people the opportunity to go to the next level in your membership is super important. Because, the biggest myth in membership is that people stay forever. Not everyone is like Jeff is ho is paying us forever out if appreciation - even though he has out-grown the Flip Your Life space.

Jeff did stay actively in that space because we were consistently three steps ahead of where he was at in his journey. We were still servicing beginners. We do a really good job at getting people to hundreds of members. Now, the whole goal of Membership Masters is that ascension when you start getting thousands of members and millions of dollars.

Jeff is doing a great job of this for the teachers in his membership by stair-stepping them!

I even saw this one time with an agility membership for dogs. Then, it ascended them into competition-level learning.

There is always a next-level learning. You need high-ticket stuff, you really do. Annual sales come in great here. You give a discount and get more money up-front. You go fuel ads to make more members.

The thing is you have to have multiple recurring products. That’s the biggest mistake I see people make in their membership. It’s about keeping them with you forever it’s not about keeping them in that same  thing forever.

That’w hat happened with Membership Masters. People kept asking for something they can get and hold them accountable every single day. So with the paper newspaper I wrote down 30 bulleted points of what I’m going to do every day this month and I just started selling that. It was the perfect way to ascend people that had simply outgrown the Flip Your Life Community and wanted to keep growing into a business that made millions of dollars or gotten several thousands of members.

Now - Jeff can not only just sell to teachers he can sell his product to entire schools! So instead of having the individual teacher paying his monthly membership site price, his high-ticket would be selling to that entire school district. If schools get an allowance of $50,000 to buy books for their schools and now Jeff can sell to them for $30,000 for digital content and give them more value at the same time.

There is always somewhere else to take people!


Vision and your art is everything to your membership.

You have got to move the way your membership is run. You have got to go from membership owner + leader of the community to leader of the community + CEO of the team that is going to help people win. Making the big visions and decisions.

I learned something from Russel Brunson recently that says vision and your art is of the upmost importance to your online business. You have to change roles and hats, you have to become the CEO and leader but you ca also divide that up. If it takes you too long and takes away form your art. For some people their art is being the CEO, managing the team, people like Jeff. Jeff is the best person at building teams and getting stuff in place, juggling 16 balls at the same time.

For me, my art is casting vision and speaking. Another part of my art is solving immediate problems. That was one thing I really loved about coaching football. I’ve seen so many business now that i solve a missing link. I want to look at high-level vision stuff not just for us but for other people.

Someone is relying on you. If you want to become a Membership Master you have to embrace that role as leader, even if that means you have to hand it off. You can’t lead the 5,000 by yourself. If you hand it off now the people still get served.


Everyone getting to be as selfish as possible is the goal.

There is no better feeling than getting messages and hearing how you’ve changed someone’s life for the better.

Thats what you’re really making your membership for: whatever problem you solve you want to solve that problem and remove part of the burdens of life from everybody in your membership. Life is hard and every little thing that everybody in your membership - that’s going to have a magnifying ripple for their family, friends, everything!

It’s not just, “oh I made some content and I’m charging $47/month.” Part of it is you’ve got to eat too. If you’re working for money, you might as well change the world in the process.

A friend of mine in one of the masterminds I’m in says that his favorite agreements and products his favorite situation is where everybody gets to be as selfish as possible and that’s good.

The person is being selfish - they want their time back after school. Right? That’s cool because why do they want that? They want their time back!

You spend years and years learning your skills, you created it and put your time in. You should get paid for it too, be selfish too for you and your family. But how much better is it when we all do it together and win together?

I think that’s a big threshold that you have to cross as a CEO or high-level membership owner: knowing that you will do whatever is in your power to make sure that that is possible for every single person in your membership.

As far as retention goes that’s your retention right there. You have to have that mindset at all times!


How to slow down churn. 

I look at churn on a monthly basis because eventually everything becomes zero. You always have to replenish your membership. People too often think that you get a customer and they never quit and that’s just not true. Sales and marketing are always the first half of it and then your monthly revenue is the back half and you have to replace at least one more than you lost every month.

Jeff’s churn in amazing at only 2.5-4% each month! Most peoples’ churn is between 7-15%.

One of the tactics Jeff uses is a quarterly membership. Because the one thing about education is that teachers sign-up to memberships like Jeff’s to save time. The problem is they can purchase something and never open it. By making the quarterly option it forces the teachers to use it in those three months. Even if they only use it twice in those 90 days, it causes them to re-think getting rid of it. Jeff has found that the quarterly and annual memberships will always reduce churn rate.

How do you reduce church on monthly memberships?

If you’re got 1,000 people paying you $50/month, let’s say they stay for two months that’s $100,000. If you can just get it to three months that’s $150,000!

Just going live, talking to people once a month, it reminds people that this is real. There’s always three parts of a membership: curated content, community, and leadership. When you add one thing to show up and at the end you say, “on next month’s live ____ I’m going to talk about _______.” You’ve immediately given them a reason to come back next month.

For the Flip Your Life community it looks like this:

  1. Future-pace.
  2. Be accessible.
  3. Try to connect with your members every single month.

Jeff says one of his best things he uses for retention is his content. He had to decide what would make him as a teacher want to stay forever. He had to think about what would provide so much value to them that they absolute could not leave. For Jeff that meant getting people in a routine. He got them in a routine of using your system every single day. He created an addiction in a good way.

Don’t just focus on retention either. Something else I’ve learned works really well is focusing on re-activation. Don’t neglect your members who had quit! I do this every quarter. I send an email to everybody that has ever quit and every time you get a raise!


Don’t spend more money than you’re making!

I was on a trip with my buddy Chandler Bolt one time. He said he called and negotiated his fees down on his payment processors by like 0.5% each. It doesn’t sound like a lot but it ended up being thousands of dollars that they spent on ads to make hundreds of thousands of dollars.

$10,000 in ads will make you a lot more money than $10,000!

If you’re selling a $1,000 course and paying $900 to get somebody to join, is it worth it? I met a guy not long ago that had three multi-million dollar funnels and he had to go get a job because he was spending more money to get them.

If I spend $1,000 to make $1,000 you might look at that and say oh that’s not good. But in a membership a certain percentage of those people are going to pay you again next month. I didn’t make only $1,000, I made the lifetime value of that. So I might spend $2,000 to make $1,000 but those people stay 6 months so that’s actually worth $6,000.

If it costs you $98 to get that person to join that’s a good place to set your price point. Let’s say you retain 75% the second month and then they stick around 10 months - you win!

The point of a membership in the beginning is to liquidated the ad spend. If you can get your point of and your up immediate up-sells to cover the cost of ads then you can’t not grow.


What positions should you hire first?

The first thing that Jeff says if he could go back in time and make a perfect membership here’s what he would hire:

  1. A personal 1-on-1 coach. He believes in investing in himself and knows the importance of this first-hand.
  2. Would advise not to outsource marketing first. because being able to be able to do those skills is important as the business owner, especially in the beginning. He first hired his content creator because he was becoming his own log-jam by not producing content fast enough. Then, he hired his graphic-designer. The way to grow the fastest is to make sure you do those things in the beginning because nobody else is going to have the passion that you are about it. These are the money tasks or the things that make you the money to hire the next person and do the next thing for you.

Hire someone to fill in your weaknesses. We all suck at things and you need to hire to fill in those gaps. If you can’t do something as well, hire it out!


If you would like to connect with Jeff Twiddy you can do so:

  • By checking out his website:


Remember to subscribe and leave us a review to the Membership Masters Podcast here on Apple Podcasts: 

You can also listen this week's full episode here on Spotify: 


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