Tropical MBA: Entrepreneurship & Founder Lifestyle

Dan interviews John Karsant, founder of Level Up Leads, a 73-person outsourced SDR agency doing about $6.5M/year revenue, built while living abroad (Argentina, now Barcelona). John shares how he found remote work early via Craigslist, then spun out a list-building service that nearly failed due to one-off sales before pivoting into full appointment setting—eventually cold calling, which raised value, doubled average sale while keeping churn steady, and enabled $15K–$20K/month packages. He explains why radical honesty wins deals, how a strong ops leader and an in-house client dashboard improved transparency, and which metrics matter most (dial-to-connect, meetings booked, show rate, and pipeline movement).

In this episode:

John discusses hiring ahead of the curve

How he compensates reps based on client retention

The decline of email outreach

John’s inbound engine that drives 80–90% of leads

Practical AI uses for role play training, transcript analysis, playbooks, and script generation

The value of an experienced CEO coach

John’s approach to investing and family life

Thanks to this week's sponsor Wayfront — the AI-ready operating system for productized agencies. One client portal. One team dashboard. All your data, AI-accessible. TMBA listeners get an extra free month on top of the trial at wayfront.com/tmba.

Links:

Level Up Leads

More Business Resources

Upcoming DC Events

🎙️ Tropical MBA is a podcast for entrepreneurs building location-independent businesses. 🔔 Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle.

Hang out exclusively with 7+ figure founders in DC BLACK

https://dynamitecircle.com/dc-black

Chapters:

(00:00:33) Guest Intro Story

(00:02:11) Argentina Remote Leap

(00:04:24) Barcelona Founder Life

(00:05:24) Time Management Abroad

(00:07:37) Business Idea Origins

(00:08:47) Pivot To Cold Calling

(00:12:17) Honest Sales Edge

(00:12:48) Ops Systems Dashboard

(00:14:27) Metrics And Financials

(00:18:12) Retention Based Pay

(00:21:44) Outbound Shifts And Inbound

(00:24:26) AI Workflows For SDRs

(00:28:43) CEO Coaching And Hard Stuff

(00:31:32) Personal Finance Investing

(00:31:16) Life Outside Work Dadhood

(00:38:58) Ideal Clients And Wrap Up

CONNECT:

Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses.

Email [email protected]

PLAYLIST:

The $10K Projects You Never Do (AI Just Changed That)

How to Build a 6-Figure Digital Business with Claude Code

We Got Claude-Pilled

Is 2026 the year you finally run paid ads? Something shifted at DC Mexico this year — more founders than ever are seriously considering paid ads as their next acquisition channel. Between AI making creative cheaper to produce and competitive research easier to do, the barriers are lower than they've been.

Max Sinclair has run a paid ads agency for eight years. In this episode he breaks down what actually works for founders spending under $30K a year — how to start, what to expect, and whether it's even worth it for your business.

Plus: how Max used AI to turn his agency's internal tools into a product, and what that transition looks like in practice.

Guest: Max Sinclair — Snowball Creations & SaaS Ads Studio

Sponsor: wayfront.com/tmba

Thanks to this week's sponsor Wayfront — the AI-ready operating system for productized agencies. One client portal. One team dashboard. All your data, AI-accessible. TMBA listeners get an extra free month on top of the trial at wayfront.com/tmba.

Links:

Business Resources

Upcoming DC Events

🎙️ Tropical MBA is a podcast for entrepreneurs building location-independent businesses. 🔔 Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle.

Hang out exclusively with 7+ figure founders in DC BLACK

https://dynamitecircle.com/dc-black

CHAPTERS:

(00:00:00) Welcome and Sponsor

(00:00:52) Episode Setup Paid Ads 2026

(00:02:54) Meet Max Sinclair

(00:03:13) Why Ads Feel Mental

(00:04:21) Beginner Tip Product Fit

(00:07:12) Picking Channels S Tier

(00:11:52) Intermediate Trust Algorithms

(00:15:07) Creative Workflows Win

(00:17:34) Advanced Scaling Strategy

(00:19:37) Small Budget Remarketing

(00:21:15) DIY Learning Roadmap

(00:24:22) Wayfront Sponsor Break

(00:25:47) Agency Sales Mastery

(00:30:19) Agency Pricing Models

(00:32:41) Pivot to AI and SaaS

(00:38:49) AI Native Team Systems

(00:41:26) Biggest Financial Lesson

(00:43:57) Wrap Up and Resources

CONNECT:

Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses.

Email [email protected]

PLAYLIST:

The $10K Projects You Never Do (AI Just Changed That)

How to Build a 6-Figure Digital Business with Claude Code

We Got Claude-Pilled

Dan and Ian are joined by Jeff Picaro of meetwingman.com to recap lessons from the DC Mexico event and share five trends for 2026 in bootstrapped, location-independent businesses.

In this episode:

• Why organic traffic is rebounding and how legacy publishers can compound results via Google, LLMs, and AI repurposing

• Why companies with strong SOPs and systems are translating fastest to AI-enabled workflows and higher margins (especially agencies)

• How org charts may shift from pyramids to circular, data-centered “hive mind” models with new technical and client-facing roles

• Why many founders who started with AI-driven layoffs are rehiring as capacity and demand expand

• Why bootstrappers should consider going upmarket, raising contract value, and pursuing bigger customers and deals.

Thanks to this week's sponsor Wayfront — the AI-ready operating system for productized agencies. One client portal. One team dashboard. All your data, AI-accessible. TMBA listeners get an extra free month on top of the trial at wayfront.com/tmba.

Resources mentioned:

Jeff Picaro

E-Myth Revisited by Michael Gerber

Work the System by Sam Carpenter

The 4-Hour Workweek by Tim Ferriss

Jack Dorsey's blog post on the circular org chart (published during Block layoffs)

Supabase

GitHub

More Business Resources

Upcoming DC Events

Tropical MBA is a podcast for entrepreneurs building location-independent businesses. Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle.

Hang out exclusively with 7+ figure founders in DC BLACK

https://dynamitecircle.com/dc-black

CHAPTERS:

(00:00:00) Welcome and Guest Intro

(00:00:59) Why Events Spark Growth

(00:02:45) Trend 1 Organic Returns

(00:07:25) Trend 2 Systems Win

(00:13:02) Trend 3 Org Charts Shift

(00:17:22) Sponsor Wayfront Break

(00:18:48) Trend 4 Layoffs to Hiring

(00:25:54) Trend 5 Go Upmarket

(00:32:23) Wrap Up and Takeaways

(00:34:46) Outro and Resources

CONNECT:

Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses.

Email [email protected]

PLAYLIST:

The $10K Projects You Never Do (AI Just Changed That)

How to Build a 6-Figure Digital Business with Claude Code

We Got Claude-Pilled

Dan and Ian just got back from DC Mexico — 4 days in Mexico City with 200 founders, a third of whom run $1M+ businesses.

Three ideas worth sitting with:

Reading about something is useful. Watching someone implement it is better. Doing it yourself, beside someone else doing it too, is where things get real.

Networking gets a bad reputation — and maybe it deserves it. But sharing a real experience with someone who's solving the same problems you are? That's where trust gets built.

And trust, right now, might be the most valuable thing a founder can have.

In this episode:

• Why reading and podcasts only get you so far

• What made the DC Mexico AI Build Lab different from any workshop they've attended

• The difference between networking and shared experience (and why it matters)

• How the attention economy is shifting — and what's replacing it

• How to get the most out of any room you're in

Thanks to this week's sponsor Wayfront — the AI-ready operating system for productized agencies. One client portal. One team dashboard. All your data, AI-accessible. TMBA listeners get an extra free month on top of the trial at wayfront.com/tmba.

Links:

More Business Resources

Upcoming DC Events

Tropical MBA is a podcast for entrepreneurs building location-independent businesses. Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle.

Hang out exclusively with 7+ figure founders in DC BLACK

https://dynamitecircle.com/dc-black

CHAPTERS:

(00:00:13) We are back

(00:02:40) Mexico City Impressions

(00:05:33) DC Mexico Event Breakdown

(00:07:14) Community Stats And Culture

(00:11:33) Reflection One Get Results

(00:17:07) Reflection Two Trust Economy

(00:23:05) Our sponsor “Wayfront”

(00:24:24) Reflection Three Shared Experience

(00:29:09) Quick Hits AI And Acquisitions

(00:30:43) Optimism And Next Events

(00:32:33) Wrap Up And Sign Off

CONNECT:

Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses.

Email [email protected]

PLAYLIST

The $10K Projects You Never Do (AI Just Changed That)

How to Build a 6-Figure Digital Business with Claude Code

We Got Claude-Pilled

Most founders already know what's wrong with their business. The fix is usually simple but scary.

So instead of doing the one hard thing that would make everything else easier, they stay busy. It feels like progress. It isn't.

In this episode, Dan walks through the 7 questions he uses in $1,000/hour coaching calls — the ones that make the real problem impossible to ignore. And he shows you how to run the same audit on your own business using AI as your thinking partner.

In this episode:

• The simple but scary problems that show up in almost every business

• Why most founders are spending money on 'hopeful outcomes' — and how to stop

• The pricing question that reveals whether you actually believe in what you're selling

• How to use AI as a founder (hint: context first, questions second)

• What does your answer to 'how would you 2x in 90 days?' reveal about your business

Resources mentioned:

The 7-Question Business Audit

The Complete Business Diagnostic

More Business Resources

Upcoming DC Events

Tropical MBA is a podcast for entrepreneurs building location-independent businesses. Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle.

Hang out exclusively with 7+ figure founders in DC BLACK

https://dynamitecircle.com/dc-black

CHAPTERS

(00:00:00) The local business story — same problems, every time

(00:04:23) AI as a thinking partner — and why context is everything

(00:07:30) Q1: What is the ROI on your biggest expenses?

(00:11:22) Q2: Where did your last 10 customers come from?

(00:12:43) Q3: If you had to raise prices 20% tomorrow, how would you?

(00:14:15) Q4: Do you have a product your best customers can pay 3–10x more for?

(00:14:35) Q5: Who owns which decisions — and is it written down?

(00:16:38) Q6: What are you doing that isn't sales or delivery?

(00:19:16) Q7: How would you 2x revenue in 90 days?

(00:22:44) Bonus: What is your business actually worth?

(00:23:49) Closing: The hard thing that makes everything else easier

(00:24:41) Community & events: Mexico, Barcelona, Bangkok, New York

CONNECT:

Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses.

Email [email protected]

PLAYLIST:

The $10K Projects You Never Do (AI Just Changed That)

How to Build a 6-Figure Digital Business with Claude Code

We Got Claude-Pilled