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38 Lessons My Mastermind Clients Learned In March 2025

Monday, April 21, 2025 / Rich Webster / Watch on YouTube / Listen to podcast​

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My mentorship clients pay me $12k a year (minimum) to help them grow their business.

We meet two times a week for 2-4 hours and go deep on topics like leads, sales, pricing, marketing, clients, content, systems, mindset, and more.

This week I tried something new…

I took all of our call transcripts from March (28 HOURS of calls) and broke them down into 38 value-packed insights.

I’ve split the lessons into 9 categories for easy navigation.

I’m not holding anything back here.

Let me know if you like the format, if it resonates, I'll do this monthly.

And if you want to hear me explain each of these in more detail, watch the full 90 minute YouTube video here.

Enjoy!

👥 Leads

1. Two types of past client outreach

Reaching out to past clients is one of the easiest ways to make more money.

But there are two types of past clients:

1️⃣ DIRECT - They pay you directly

2️⃣ INDIRECT - They connect you to someone who pays you

Your approach must be different for each.

Most people get this wrong.

For DIRECT leads, come to the table with ideas.

Don’t just ask if they have work.

“I was thinking about you (not in a creepy way) and had some ideas about XYZ…”

This shows you’re there to do the thinking, not asking them to figure out how to use you. (see more below)

For INDIRECT leads, make it EASY for them to help you.

Try: “I’ve been reflecting on my business plans and would love more clients like you. Know anyone who might benefit from what I do in the next 90 days?”

Simple, specific, and low-friction.

2. How to pitch past clients the right way

Here’s outreach script for DIRECT leads:

“I was thinking about you recently. I have some ideas about [achieving outcome they want]. Would you be open to hopping on a call this week?”

Don’t oversell.

Just get the meeting.

When you get to the meeting, have a locked-and-loaded offer ready for them, but START by exploring their current problems and goals.

What you’ll often find:

New priorities have emerged since you last worked together that are MORE important than what you initially planned to pitch.

Here are the steps to do it:

1. List all past clients
2. Rank by quality of relationship
3. Create personalized offer (based on quality of relationship)
4. Reach out with script

💸 Sales

3. 3 simple changes to dramatically improve sales calls

1. Set clear expectations at the start

Set expectations EARLY: “The goal of this call is for us to decide if it makes sense to work together. If I think we can, I’ll make you an offer. If not I’ll refer you or give you value. Are you comfortable with that?”

1. Summarize their problems back to them

“So your most important goal is X, and your main challenges are Y and Z. Is that correct?”

If this is right, the YES will be resounding.

If it’s wrong, dig deeper.

1. The “conceptual yes”

Ask if they’re ready to move forward BEFORE discussing price.

The conceptual YES is more important than the financial YES.

Before discussing money, make sure they’re excited about the IDEA of working with you.

“Based on what we’ve discussed, are you ready to move forward?”

If they’re not excited about the solution without knowing the price, they won’t be excited after.

4. It’s never price.

Price is NEVER the real issue.

When you get to price at the end of a sales call, its already decided.

It’s not the number.

It’s everything that happened (or didn’t happen) BEFORE you stated the price.

Build trust first, then the money conversation flows naturally.

If people really see the value in something, they find a way to make it work.

5. “Do you trust me?”

The most powerful question you can ask a potential client:

“Do you trust me?”

It cuts through the noise and gets to the heart of the relationship.

If trust isn’t there, nothing else matters.

And when they say yes, price becomes secondary.

6. You don’t have to close clients

When you approach sales conversations with genuine detachment from the outcome, prospects can feel it.

Paradoxically, this makes them MORE likely to work with you.

Clients can sense desperation.

When you genuinely approach calls thinking “I don’t have to close this,” you close MORE deals.

7. Shut up

When saying your price, look the client in the eye and then SHUT UP.

Don’t look away.

Don’t fidget.

Don’t apologize.

Don’t justify.

State the price clearly, then wait.

The silence is uncomfortable, but necessary.

8. Two headed dragon

Two-person sales calls are the “two-headed dragon” of selling.

Even if both people want to say yes, they often won’t commit without conferring privately first.

Address this upfront:

“Can we talk openly here, or would you prefer to discuss privately after?”

9. The better your get at sales, the less it feels like sales

The best salespeople don’t feel like they’re “selling” at all.

They’re having authentic conversations to determine if there’s alignment between what the client needs and what they offer.

The goal isn’t to get a yes—it’s to decide if you SHOULD work together.

10. The two games

There are TWO games happening in every organization:

1. The company’s game (metrics, profits, outcomes)
2. The personal game (individual goals, relationships, recognition)

You must play BOTH to become indispensable.

The company game is obvious - ROI, profits, outcomes.

But the personal game?

That’s where relationships are built.

Understanding what your contact personally cares about (promotion, looking good to bosses, job security) is how you move from vendor to partner.

Want to be truly indispensable?

Become BFFs with your initial point of contact

They’re often the gatekeepers between you and the organization.

If they feel you’re taking away from their work rather than adding to it, you’re toast.

Make them your biggest champions.

2 real examples:

1. One client cared deeply about looking good to his board of directors.

Why? He planned to leave in 3-5 years and saw board relationships as his golden ticket to something better.

Knowing this changed how I positioned my work with him completely.

1. A marketing manager who wanted to be promoted to comms director.

I gave her advice on what to take credit for (including my work!) and made her job easier.

Result? She’d never suggest cutting me from the budget. I was valuable to HER, not just the company.

📣 Marketing

11. How to write sales copy

The goal is to create content that makes your ideal client think:

“This person is in my head. They understand exactly what I’m going through better than I could articulate it myself.”

This is the most powerful marketing you can do.

The only way to nail this is to TALK to people.

And you have to spend the time to get it right.

It took me over a year to nail the articulation for the Lab video.

12. Needs vs. wants

When positioning your business, you must balance what clients NEED with what they WANT.

People buy what they want, then discover what they need after.

If you only talk about what they need (but don’t yet know they need), they’ll never become clients to discover you were right.

13. Send more emails

When you send more emails, you make more money.

If someone unsubscribes from your email list because you email too often, they probably weren’t going to be a customer anyway.

Promote your newsletter/services frequently.

The correlation to cash is direct.

14. Radical empathy

When pitching your services, put yourself in the client’s shoes.

Agency owners care about:

• Making money
• Quality work
• Not having to micromanage
• Independent thinking

Speak to THEIR needs, not yours.

15. High end marketing

For luxury brands and high-end services, less is more.

Louis Vuitton doesn’t need to explain why their handbags are worth it.

They just show it.

The higher-end your brand:

• The fewer words you need
• The fewer buzzwords you use
• The more understated your approach

16. Friction in your funnel

Friction is designed to increase or decrease call volume.

• More barriers and friction = less calls, higher close.
• Less barriers and friction = more calls, lower close.

The ultimate friction is showing the price.

For my agency I wanted as few calls as possible, b/c I was only looking for 1-2 perfect clients a year.

So my friction was through the roof:

• Minimum rate: $60k
• Referrals only
• Calls one day a week

🤝 Clients

17. Dealing with client delays

When clients constantly delay projects, you have two options:

1. Structure deals so delays = more money for you.
2. Set clear expectations upfront with consequences.

Pro tip: Put timeline commitments in your contract with specific language about client-caused delays.

18. Intention: Years

When starting client relationships, be explicit about your intentions:

“I want to work with you for YEARS, not just one or two projects.”

No one says this!

It immediately sets you apart and shows you’re invested in their long-term success.

💰 Pricing

19. Fully booked is bad

“Being fully booked is a signal from the market that you’re not charging enough.”

This is one of the most powerful mindset shifts for service providers.

If you’re constantly maxed out, you’re leaving money on the table.

Raise your prices until you hit 50-75% capacity.

20. Bringing the future into the present

Most entrepreneurs create an imaginary timeline:

“Eventually I’ll charge higher rates, but not today.”

95% of raising your prices is simply COMMITTING to living as your future self NOW.

There’s no magic testimonial that will suddenly make clients throw money at you.

The only thing that changes is your willingness to say the number with conviction.

21. Cheap clients

Bending over backwards for low-paying clients creates resentment.

As you raise your standards and prices, some clients won’t come along for the ride.

That’s not just okay - it’s necessary.

Make space for clients who value your work at its true worth.

🎥 Content

22. Millenial content mistake

For millennial content creators: Stop introducing your topic!

Don’t do this: “Today I’m going to talk about XYZ”

Gen Z knows the power of jumping straight to the point.

Lead with your most controversial or counterintuitive point.

And always tell viewers exactly what they’ll get:

“3 tips for X in 60 seconds” beats “Talking about X today.”

23. When something works, do more

The biggest mistake creators make:

They experiment until something works, then immediately move on to try something new.

When you find a format that resonates, MILK IT.

Don’t reinvent the wheel every time.

Double down on what’s working and create variations of that winning formula.

We test to find winners.

24. Content system framework

Your content creation process should follow this pattern:

1. Experiment manually until you find what works
2. Create templates for the winning formats
3. Identify your “zone of genius” (the 20% only YOU can do)
4. Delegate everything else

Most creators never get past step 1.

25. Lead magnets

Lead magnets are your bridge between social media (rented land) and your email list (owned land).

The best lead magnets are so valuable people would pay for them, but you give them away free.

And they MUST align with what you actually sell.

Don’t bait and switch.

For lead generation, your social media should be your DISCOVERY platform, while your email list is your RELATIONSHIP platform.

26. AI - volume

My biggest bottleneck as a solopreneur? Volume.

AI now offers a clear path to 5-10x my output without increasing my time investment.

The key: Use AI to expedite creation, not to THINK for you.

The source material must still be uniquely yours.

27. The best content captures what you’re already doing

The best content system is one that captures the value you’re ALREADY creating.

I generate 4-6 hours of original thinking every week on client calls.

That’s my raw material.

The key was finding a way to extract insights without having to relive every conversation.

Content creation hack:

Use AI to process your call transcripts and extract key insights.

Then build a system where 2 hours of writing creates all the content you need for a week.

The goal isn’t to create content from scratch—it’s to package the thinking you’re already doing.

🛠️ Systems

28. “Defining done” for building systems

When building systems, start with the outcome and work backwards.

Ask yourself:

• What does “done” look like?
• What am I NOT doing? (be ruthless here)
• What’s the 20% only I can do?
• What can be templated and delegated?

This clarity changes everything.

For me, that’s:

• 5 threads posts daily
• 2-3 IG posts weekly
• 1-2 reels weekly
• 1 long-form content piece

Define “done” first, then build systems to achieve it consistently.

🎯 Big Picture

29. 4 stages of solopreneurship

Your next move depends on where you are:

• Under $100K: Master your craft
• $100K-$250K: Choose your path (fulfillment vs. marketing)
• $250K-$500K: Build systems & delegate
• $500K+: 2X or design yourself out

30. Where the market is going in 2025

The market is shifting:

• Information is cheaper than ever (thanks AI)

• Generic courses are losing value

• Personalized expertise is becoming MORE valuable

The future belongs to those who can provide context, discernment, and human judgment—things AI cannot replicate.

31. Fire your team and reconnect

Sometimes the best business move is to fire your team and reconnect with your craft.

It sounds counterintuitive in a world obsessed with scaling, but bigger isn’t always better.

When you’re doing your best work, enjoying it, and clients are paying premium rates - you’ve found your sweet spot.

Then rebuild with leverage and scale.

32. Don’t use debit cards

Just had my debit card charged $1,300 by an AI company I barely use.

Someone hacked my account, upgraded to their highest tier, and burned through all the credits in 2 hours.

Lesson: NEVER put debit cards where credit cards should go.

When things go wrong, it’s the bank’s problem, not yours.

🧠 Mindset

33. The biggest pain as an entrepreneur

The most painful part of growth isn’t lacking awareness of what to do.

It’s KNOWING what you should do and not doing it.

That middle space—where you’re aware but not acting—is where the real discomfort lives.

This is where transformation happens or stalls.

34. Fear fuel

Fear is amazing fuel.

It works.

That’s why it’s so hard to let go of.

But using fear as motivation comes at a cost—to your wellbeing, creativity, and sustainability.

35. Obstacle is the way

Outreach is the path most entrepreneurs avoid—and precisely what they need most.

The resistance you feel toward reaching out is the exact indicator you should be doing it.

The obstacle is the way.

The thing you’re avoiding is usually the thing that will move you forward fastest.

36. “What am I avoiding right now and why?”

The most powerful question for entrepreneurs stuck in their head:

“What am I avoiding right now and why?”

Morning pages (writing stream of consciousness first thing) can be transformative for uncovering these blocks.

37. Shiny objects

When considering a new business direction, ask yourself:

“If I had 50 new clients in my CURRENT business, would I still be exploring this new opportunity?”

If the answer is no, you’re probably trying to solve a revenue problem, not pursuing a strategic evolution.

38. Hand grenades

The most dangerous moment for entrepreneurs is when things are working but growth is slower than you’d like.

That’s when the hand grenade appears—the temptation to blow up what’s working to chase something new.

Don’t pull the pin.

Double down on what’s working.

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That's it! If you want be a part of the group where these lessons emerge, check out the Lab below. If you're earlier in your journey, start with 🏖️How to Work Less.