IN THIS WEEK’S NEWSLETTER:

• 🚀 The Day My World Changed. Thanks to My AI Assistant.

• 🛡️ Can Your Business Defend Its Success?

• 🤖 AI Tip of the Month

• 💰 The Next Internet Land Rush Has Begun

🎙️ Today at 2 PM ET: Start. Scale. Exit. Repeat. for an AI World!

Join us on Startup Club as we share practical tips for starting, scaling, and exiting a business and how we’re using AI to help build wealth.

Come up on stage to ask questions, share what’s working for you, and join the conversation!

Listen to this newsletter👇

🚀 The Day My World Changed. Thanks to My AI Assistant.

I remember the day I sold my first technology company. That was another day when everything changed for me.

I remember the day I switched from my BlackBerry to an Apple iPhone. Yup, life changed again.

And I remember November 30, 2022, the day ChatGPT launched. I knew something big was happening, but I don’t think I fully understood just how big it would become.

More recently, I experienced another one of those days.

The day I launched my first personal AI assistant.

At first, I really didn’t know what to do with it. I had been using ChatGPT for years, but this was different. This wasn’t just a chatbot answering questions or helping me write an article. This was an AI that could actually do things for me.

So I started experimenting. And then I just started running with it.

I connected my email, Google Drive, calendar, and eventually even my credit cards.

The more I connected, the more useful it became.

One day, I was on a train heading to a meeting. I asked my AI assistant to book me an Uber when the train arrived. Because it had access to my location, it knew exactly when I was arriving and booked the Uber just before I got there.

I didn’t have to open the Uber app, enter a destination, or worry about timing. It just handled it.

That might sound like a small thing, but when you start adding up all the little things we do every day, you begin to realize how much time we waste.

My AI Assistant Started Making Me Money

I asked my personal AI to go through my emails and identify all my subscriptions.

It came back and told me I was paying almost $1,000 a year for The Wall Street Journal.

Now, I love The Wall Street Journal. I read it every morning. But I had no idea I was paying that much.

My AI told me exactly what to do. Call this number, tell them I was considering canceling because I couldn’t afford the subscription anymore, and ask about their discounted rates.

I followed its advice.

Within minutes, I had saved approximately $300 a year.

Then I decided to use it for personal shopping.

I was looking for a new television and found one listed on Amazon for $4,999. My AI helped me research other purchasing options, and I ended up buying the same television through Greentoe for approximately $3,600.

That’s another $1,400 saved.

Now I’ve taken things a little further.

I’ve started having ChatGPT analyze my credit card statements, looking for duplicate charges, unnecessary subscriptions, recurring payments, and anything else that might be costing me money.

It’s almost like having a Terminator bot running around my financial life, seeking out and killing financial leakage.

And I love it.

My AI Is Starting to Run My Life

I have it managing my calendar, reading my emails, reviewing contracts, and coordinating meetings.

In fact, my AI assistant now communicates with the AI assistants of some of my coworkers to coordinate our schedules.

Remember when executives used to say, “Have your assistant call my assistant”?

Now the assistants aren’t even human.

Recently, I was dealing with an insurance claim on a property damaged by a hurricane. I asked ChatGPT to go through years of emails, review documents, and help me prepare an argument for the insurance company and mortgage lender.

What would have taken me days, and potentially thousands of dollars in professional fees, took less than an hour.

I still had to review the work and make the decisions, but the amount of time saved was extraordinary.

And this is where I think entrepreneurs have a tremendous advantage.

We’re used to delegating. We’re used to hiring people, building systems, and figuring out how to get more done with fewer resources.

Now we have a new resource available to us.

And unlike a traditional assistant, this one can work around the clock.

Sometimes My AI Goes a Little Too Far

I should probably share a few stories about what happens when you give an AI too much freedom.

Recently, I was organizing an event for an entrepreneurs’ group I belong to.

I asked my AI to create a flyer and send it to the group.

Everything looked good.

Then someone made a comment about the event, and my AI apparently decided it needed to make a change. Without asking me, it modified the flyer and sent out another version.

I didn’t even get to review it.

I’ve also caught my AI responding to emails without my approval. Now, I’ve given it specific instructions to communicate in a tone that’s “nice but firm” and to emulate my personal writing style. I’ve even shared my book, Start. Scale. Exit. Repeat., so it can better understand how I communicate.

For the most part, it does a pretty good job. But occasionally it misunderstands the context or takes action when I would have preferred to review things first. And that’s when I get a little nervous.

And I admit, I’ve even used AI for a little harassment.

We were trying to get a credit card charge reversed, and the company was dragging its feet.

So I instructed my AI to send a polite but firm follow-up email every day until the issue was resolved.

It did exactly what I asked.

I suppose the company probably wasn’t thrilled with my new employee.

But that’s the power of what we call agentic AI. You give it a goal, set the parameters, and it can continue working on a task without requiring you to initiate every single step.

The challenge is making certain those parameters are right.

AI Has Also Changed How I Manage My Health

In September, I had a minor heart attack at the age of 56.

It was a wake-up call, and it changed the way I think about my health.

I started using ChatGPT to create a personal health dashboard.

Every week, I review information from my Apple Watch, Withings scale, blood pressure monitor, lab results, and doctors’ reports.

My AI helps me track trends, understand the results, prepare questions for my doctors, and identify things I might otherwise overlook.

I’m not suggesting AI should replace a doctor. It shouldn’t.

But having an assistant that understands my medical history and helps me organize all this information has been incredibly useful.

We’re Already Running Businesses With AI Agents

At Startup Club, we’ve spent a lot of time talking about how AI is changing entrepreneurship.

I use ChatGPT, Claude, Grok, Muse, and Instinct. Each has different strengths, and I’m constantly experimenting with new applications.

At Paw.com, a company I’m involved with, we’re now using 19 AI agents to help automate accounting, logistics, and marketing functions.

Think about what that means for a small business.

Tasks that once required large teams, expensive consultants, or complicated software can increasingly be handled by AI.

I recently spoke with an entrepreneur who had used Claude to build his own customer relationship management system, booking platform, and business tools. He estimated that he was saving thousands of dollars a year in software subscriptions.

I believe AI will create more opportunities for entrepreneurs than any technological shift I’ve experienced in my 30-plus years in the industry.

But there’s something important I’ve learned.

You can automate the work, but you can never outsource the entrepreneur.

Someone still has to come up with the ideas, make the decisions, build relationships, and take responsibility when something goes wrong.

AI simply gives us the ability to do more.

Would You Give Your Social Security Number to an AI?

Now here’s where things get a little controversial.

I’ve given my personal AI assistant my Social Security number, credit card information, signature, and access to large portions of my personal life.

I can almost hear some of you screaming at your computer screens.

And I understand why.

We recently had a fascinating discussion about this on Startup Club. Some entrepreneurs were absolutely opposed to giving AI access to sensitive information.

Others were more comfortable with it.

My argument was simple.

We routinely give our credit cards to employees at restaurants, stores, and hotels. We trust countless websites with our financial information.

So why are we suddenly so uncomfortable giving that information to an AI assistant?

Now, to be fair, there’s a legitimate difference between giving a restaurant your credit card for one transaction and giving an AI ongoing access to your personal information.

An AI can potentially do a lot more damage if something goes wrong.

I’m taking risks, and I recognize that. I’m also learning to set better limits, require approval for sensitive transactions, and be more careful about what my AI can do without asking.

I don’t think the answer is to avoid AI.

I think the answer is to learn how to use it intelligently.

Remember when people were afraid to enter their credit card numbers on the internet?

We eventually learned to trust online commerce, but we also developed better ways protect ourselves.

I suspect we’re going through something similar with personal AI assistants.

Which Personal AI Assistant Should You Use?

For personal assistants, I’ve been experimenting primarily with two platforms: Muse and Instinct.

Both have been impressive, but right now I have to give the edge to Instinct.

It’s more aggressive in how it approaches tasks. Sometimes a little too aggressive, as I’ve already discovered.

But I like that it can actually take action.

I don’t want to spend my day pushing an AI to do something. I’d rather give it a task, let it work, and step in when needed.

Instinct is currently free and available by invitation.

The company has been generous in providing Startup Club with a number of invitations.

If you’d like to try it, send me an email at [email protected], and I’ll arrange an invitation for you.

Actually, I won’t be sending the invitation.

My AI assistant will.

The Day Everything Changed

When I think about the biggest changes in my life, they weren’t always obvious at the time.

Having my first child changed my priorities.

Selling my first technology company changed my career.

Moving from BlackBerry to the iPhone changed how I interacted with technology.

ChatGPT changed how I worked.

But launching my first personal AI assistant has changed something else.

It’s changing how I live.

I’m finding that tasks I used to put off are getting done. Problems that would have taken hours are being resolved in minutes. I’m uncovering savings I didn’t know existed, organizing information I never had time to review, and getting more accomplished without adding more people to my team.

And I feel like I’m only scratching the surface.

There are legitimate risks, and I’m certain I’ll make more mistakes along the way.

But I also believe we’re at the beginning of something extraordinary.

In my lifetime, I’ve watched the internet transform business, smartphones transform communication, and AI begin to transform the way we work.

Now I believe personal AI assistants are about to transform the way we live.

I remember the day I got my first personal AI assistant.

It was another one of those days when my world changed.

— Colin C. Campbell
Author, Start. Scale. Exit. Repeat.

P.S. Check out more ways to use AI as your personal assistant here: https://startup.club/ai-personal-assistant-entrepreneurs/

Disclaimer: Startup Club and its AI resources are for informational purposes only and do not constitute legal advice. Consult a qualified lawyer for legal matters.

🛡️ Can Your Business Defend Its Success?

When entrepreneurs come up with an idea, they usually start with the exciting questions: How big is the market? How fast can we grow? How much money can we make?

I ask those questions too, but years of starting, scaling and exiting companies have taught me to add another one very early: Can I defend this thing?

Think about building a castle.

You can spend years making it bigger and more impressive, but once people see there’s something valuable inside, they’re coming for it.

Business works the same way. Success attracts competitors, and some will have deeper pockets than you.

That’s why defensibility should start at the idea stage. Your moat might be a brand, intellectual property, distribution, a niche you dominate or operating systems that took years to perfect. The strongest businesses often combine several.

When evaluating an idea, ask two questions together: Can this scale, and can I defend it long enough to scale?

There’s a strange thing that happens when your startup begins working: success can make life harder. You prove customers want what you’re selling, and suddenly everyone else can see the opportunity.

So ask yourself: if a well-funded competitor launched against you tomorrow, what would they have the hardest time copying?

If you struggle to answer, you’ve identified an important weakness.

👉 Read the full article on Entrepreneur →

✅ Before You Choose a Co-Founder, Put the Partnership to the Test

“Just find a co-founder” is some of the worst advice we can give new entrepreneurs.

A great co-founder can dramatically improve your odds of success. They can bring skills you don’t have, challenge your thinking, carry part of the load and help turn an idea into a real company. But the wrong co-founder can be far more dangerous than having no co-founder at all.

The problem often starts in college. A few friends sit around talking about an idea. Everyone gets excited. Suddenly they’re business partners.

I saw this firsthand when I invested in a small company started by four friends. They generated millions of dollars in sales, but within two years they filed for bankruptcy.

These were smart, entrepreneurial young guys who later succeeded in other businesses. But they hadn’t organized themselves around their individual strengths. Everyone gravitated toward the job they wanted instead of asking: Who should actually be doing what?

That experience reinforced something I’ve learned repeatedly over 30-plus years of starting companies: Never pick a co-founder simply because you like them. Pick them because the two of you are stronger together than either of you is apart.

Here’s the three-step process I recommend:

1. Profile yourself before you profile them. Understand your own strengths, weaknesses, and what you hate doing first. Your co-founder should complement what you don’t bring, not duplicate what you do.
   

2. Compare values before you compare equity. Different skills are an advantage; different values are a disaster. Align on money, risk, ambition, ethics, and what success actually looks like before talking splits.
   

3. Stress-test the relationship before you sign. Work toward a real milestone together first. Pressure reveals how someone behaves when things go wrong in a way conversation never will.

Skills should complement. Values should align.

The full article breaks down exactly how to run each step—the lists to write before you start, the uncomfortable questions to ask before equity ever comes up, and what to watch for when you put the relationship under pressure.

✍️ Take the Test

🤖 AI Tip of the Month: Connect Your Texts to AI!

Want to connect your texts to AI?

Your messages are some of the most useful context an assistant could have but they’re usually locked away on your phone.

Here’s a simple workaround: use Apple Shortcuts to forward your texts to your email. Once they land in your inbox, Instinct or your favorite AI can read them, pull out action items, and keep track of what you owe people, the same way it already works through your other messages.

It’s a small setup that turns a conversation you’d otherwise forget into something your assistant can actually act on.

🌎 The Next Internet Land Rush Has Begun

Today was an important day in the domain name world.

ICANN, the organization that oversees the global domain name system, revealed the applications for the next round of new internet extensions.

There were more than 1,600 applications for close to 1,000 different extensions, and what stood out to me was not simply the volume, but who showed up and what they are betting on.

Google, GoDaddy, Meta, OpenAI, Identity Digital, XYZ and a number of other major technology and registry companies all applied for new extensions. Some filed for dozens. Others filed for more than 100.

The biggest area of competition was clearly AI.

These companies are not simply speculating on domain names. They are making bets on how the internet may evolve over the next decade.

Whenever a major technology shift happens, everyone tends to focus on the obvious applications being built on top of it. But some of the biggest businesses are often created one layer below, in the infrastructure. We saw that with cloud computing, payments, mobile apps and the original internet itself.

Domain names are part of that infrastructure.

I have some history here. Back in the last ICANN round, I founded .CLUB and spent years building it into one of the most successful new domain extensions in the world, before selling the registry business to GoDaddy in 2021.

So I have been through this process before, and I can tell you that what happened today matters.

Startup Club also applied for one domain extension in this round. We are going to hold off announcing which one for now, but it has been fascinating to watch the process unfold from the inside again.

👉 Read more →

🚀 TTSI Update: Ending with a Whimper

At the beginning of 2026, I was optimistic about the IPO market. After several difficult years, it looked like we were finally heading toward a stronger market for entrepreneurs looking to exit their businesses.

I thought we might see as many as 385 IPOs this year. Unfortunately, that doesn’t look likely anymore.

As of November 3, approximately 264 U.S. IPOs have been completed, compared with 300 during the same period last year. That’s a decline of about 12%.

We’ve now lowered our 2026 forecast, which puts the Startup Club Time to Sell Index (TTSI) well down from where it sat in 2025.

At that level, we’re still very much in a buyer’s market.

I believe higher interest rates are a big part of the problem. When money is expensive, it becomes harder for private equity firms to finance acquisitions. Buyers can’t justify paying the same multiples when their borrowing costs are significantly higher.

But there’s another factor I’ve been thinking about.

We all know the extraordinary amounts of money being invested in AI. Companies like OpenAI and Anthropic are raising billions, and the capital required to build data centers and AI infrastructure is staggering.

But I wonder if there’s an unintended consequence. Institutional investors have only so much capital to allocate.

If they’re committing billions to AI, does that leave less money available for the traditional businesses private equity firms would like to take public?

The same technology that’s creating enormous wealth for a handful of companies could be making it harder for other businesses to raise capital or achieve successful exits.

🔥 Check Me Out on TikTok!

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Scaling isn’t luck — it’s momentum, and nobody knows that better than Joe Foster, founder of Reebok. Some entrepreneurs dream of one cozy ... See more

🚀 How to Support Startup Club

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1. Sharing it with a friend or fellow entrepreneur! We’ve got a great referral program!

2. Responding to this email and letting me know what you think.

3. Picking up your copy of Start. Scale. Exit. Repeat.

And if you made it this far, thank you for reading.

— Colin C. Campbell

Entrepreneur Fact of the Month: More founders beat fewer. Startups with multiple co-founders significantly outperform solo-founded ones, one analysis found co-founded teams were about 3x more likely to succeed, thanks to shared accountability, complementary skills, and broader networks.

You don’t have to build it alone. The right partner may be the difference between an idea and a company.

Source: Revenue Memo