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EP36: What Actually Works when Raising Money

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Getting it right the first time & setting up for success

(Recorded Live on Clubhouse November 12, 2021) 

We were joined by Lil Roberts, CEO and founder Fintech platform Xendoo, for insights into raising capital for your startup. We learned where to look and what to look for in an investor, preparing to meet with potential investors, plus Lil’s top tips for perfecting your pitch.

Moderators: Colin C. Campbell, Michele Van Tilborg, Rachael Lashbrook, Jeff Sass

Guest: Lil Roberts

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Catch the Next Wave: Why AI Timing Matters More Than Ever

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Part of Startup Club’s ongoing series exploring Colin C. Campbell’s Start. Scale. Exit. Repeat.—reimagined for the AI era. This post is adapted from Chapter 3: Catching the Next Wave Is Critical.

There’s an old saying in entrepreneurship about being in the right place at the right time. But after building multiple startups and watching countless founders succeed—or fail—it’s clear that success is less about luck and more about finding the right wave at the right moment.

Today’s wave is unmistakable.

Artificial Intelligence.

But just because AI is transforming every industry doesn’t mean every AI startup will succeed. The lesson from Chapter 3 is more relevant than ever: great founders don’t simply build great products—they build products that arrive when the market is ready.

Don’t Build Before the Wave

History is full of brilliant ideas that failed because they were too early.

The technology worked.
The founders were talented.
The execution was solid.

The market simply wasn’t ready.

Colin shares the story of Barpoint.com, an idea that let shoppers scan barcodes to compare prices and reviews instantly. Today that sounds obvious. In the early 2000s, before smartphones and QR codes became commonplace, it was simply too early. The surfboard was built—but there wasn’t a wave to ride.

AI founders should ask themselves the same question: Is the market ready for what I’m building?

AI Has Crossed the Chasm

One of the biggest concepts in entrepreneurship comes from Geoffrey Moore’s Crossing the Chasm.

New technologies are first embraced by innovators and early adopters. The real opportunity comes when they cross into the early majority and become mainstream.

For years, AI lived mostly with researchers and technical enthusiasts.

Today, that’s changed.

Millions of people use ChatGPT, Claude, Gemini, Midjourney, Cursor, Perplexity, and countless AI-powered products every day. Businesses aren’t asking whether they’ll adopt AI anymore—they’re asking how quickly.

That means the opportunity has shifted.

It’s no longer enough to build an AI model.

The winners will build businesses that make AI easier, faster, and more valuable for everyday users.

Winning Isn’t About Being First

Many founders obsess over being first to market.

Chapter 3 argues something different.

Being first matters far less than being ready when demand explodes.

We’ve seen this repeatedly in AI.

OpenAI wasn’t the first company researching language models.

GitHub Copilot wasn’t the first coding assistant.

Perplexity wasn’t the first search engine.

Cursor wasn’t the first IDE.

They won because they delivered exceptional products at precisely the moment customers were ready.

Timing compounds execution.

Don’t Force New Behaviors

One of the biggest mistakes startups make is trying to convince customers to behave differently.

People rarely change habits just because your startup exists.

Instead, the best products fit naturally into workflows customers already have. Colin points out that companies like Uber and Airbnb transformed industries without forcing customers to learn entirely new behaviors—people already took taxis and booked accommodations.

The same principle applies to AI.

Ask yourself:

  • Does this replace work people already do?
  • Does it save time?
  • Does it remove friction?
  • Does it integrate with existing tools?

If the answer is yes, you’re surfing the wave.

If you’re asking users to completely rethink how they work, adoption becomes much harder.

Make AI Invisible

One of Colin’s recurring themes is simple:

Make it easy. Market easy.

This may be the biggest opportunity in AI today.

Customers don’t actually want AI.

They want faster hiring.

Better marketing.

Cleaner code.

More sales.

Better customer support.

Less paperwork.

The companies that win won’t necessarily have the smartest models.

They’ll remove the most friction.

Great AI products make complex technology feel effortless.

Focus Before You Expand

Another key takeaway is to strive for depth before breadth.

Rather than solving everything for everyone, dominate a single niche first. Geoffrey Moore’s “bowling pin” strategy emphasizes winning one focused market before expanding into adjacent ones.

AI makes this easier than ever.

Instead of building “AI for everyone,” build:

  • AI for dentists
  • AI for real estate investors
  • AI for construction firms
  • AI for accountants
  • AI for podcast creators

Depth creates trust.

Trust creates referrals.

Referrals create momentum.

Momentum creates scale.

Every Wave Creates New Opportunities

When Colin first wrote this chapter, AI was already appearing as one of the next major technology waves entrepreneurs should pay attention to.

Just a few years later, that prediction has become reality.

But the biggest opportunities are no longer in building foundational AI models.

They’re in applying AI to industries that haven’t yet been transformed.

Healthcare.

Education.

Legal.

Manufacturing.

Construction.

Government.

Financial services.

Every major shift creates thousands of startup opportunities—not because the technology changes, but because entrepreneurs discover new problems worth solving.

Final Thought

Entrepreneurship has never been about predicting the future perfectly.

It’s about recognizing when the future has finally arrived.

AI is no longer a distant trend.

It’s today’s wave.

The founders who succeed over the next decade won’t simply build with AI—they’ll understand timing, reduce friction, solve real problems, and deliver exactly when the market is ready.

That’s how companies don’t just launch.

That’s how they scale.

Read the Book Series

This article is part of Startup Club’s series on Start. Scale. Exit. Repeat. by Colin C. Campbell, adapted for an AI-first world. In each chapter, we’re revisiting timeless startup principles through the lens of today’s rapidly evolving technology landscape—helping founders build businesses that are ready for the next wave. Check out our Chapter 2 article about taking ideas to business reality.

Decision fatigue, stress and workload – CE

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Decision fatigue, stress and workload – CE

https://www.clubhouse.com/i/decision-fatigue-stress-and-workload-ce/xtJgd9bL

Catching the Next Tech Wave in an AI World

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Catching the Next Tech Wave in an AI World

https://www.clubhouse.com/i/catching-the-next-tech-wave-in-an-ai-world/x69Qiir3

Catching the Next Wave Is Critical – CE

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Catching the Next Wave Is Critical – CE

https://www.clubhouse.com/i/catching-the-next-wave-is-critical-ce/xtJgd9bL

From Idea to Launch – The Complete Entrepreneur

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From Idea to Launch – The Complete Entrepreneur

Great businesses aren’t built on ideas alone. Learn how to validate your concept, take action quickly, and turn momentum into a real startup.

https://www.clubhouse.com/i/from-idea-to-launch-the-complete-entrepreneur/9GbHARjn

From Idea to Action in the Age of AI

Chapter 2 from Start. Scale. Exit. Repeat., adapted for today’s AI-powered entrepreneurial world

Ideas are cheap.

Execution has always been the advantage. AI just makes that more obvious.

For the past decade, entrepreneurs have obsessed over finding the perfect idea. Today, AI can generate a hundred business ideas before you’ve finished your morning coffee. It can write business plans, build prototypes, design logos, and even create marketing campaigns in minutes.

None of that matters if you never ship.

This article is adapted from Chapter 2 of Colin C. Campbell’s bestselling book, Start. Scale. Exit. Repeat. While the original chapter was written before today’s AI explosion, its central lesson has become even more relevant:

Ideas don’t create companies. Action does.

The Uber That Never Happened

Years before Uber became one of the world’s most valuable startups, my partners and I found ourselves stranded in foreign cities trying to find taxis.

We imagined an app that would use GPS to locate nearby taxis, summon one instantly, and let you watch it arrive.

We even bought the domain.

Then we moved on to another project.

Someone else executed.

That’s entrepreneurship in a nutshell.

History doesn’t reward the first person who thinks of an idea. It rewards the first team that brings it to life.

Today AI makes this lesson even harsher.

If AI helped you think of an idea, chances are it helped thousands of other entrepreneurs think of it too.

The only differentiator left is execution.

AI Is Your Accelerator, Not Your Business

Many founders treat AI like the business itself.

It isn’t.

AI is simply leverage.

Use it to validate customer demand faster.

Use it to build prototypes.

Use it to write copy, analyze competitors, summarize customer interviews, or generate your first website.

But don’t confuse productivity with progress.

You can spend weeks prompting ChatGPT without talking to a single customer.

That’s still procrastination.

The entrepreneurs who win will be the ones using AI to spend more time with customers, not less.

Share Your Idea Earlier Than Ever

Many founders still worry someone will steal their idea.

That’s almost never the real risk.

The bigger risk is building something nobody wants.

One of the first actions every entrepreneur should take is sharing the idea with people who understand the space and with potential customers who might actually buy it. Their feedback improves the idea, identifies blind spots, and often introduces the partners, mentors, or investors you’ll eventually need.

AI can simulate feedback.

Real people provide reality.

Use both.

Build Before You Feel Ready

One of the biggest changes AI has created is the speed at which entrepreneurs can test assumptions.

You don’t need six months to build an MVP anymore.

You can launch a landing page today.

Generate mockups this afternoon.

Create demo videos tonight.

Collect customer feedback tomorrow.

The barrier to building has collapsed.

The barrier to acting is still entirely psychological.

Find Your Entrepreneurial Playground

One of the best ways to move from idea to execution is by surrounding yourself with builders.

Incubators, accelerators, entrepreneur communities, and startup organizations provide accountability, introductions, feedback, and practical support that dramatically increase your chances of success. They exist to remove barriers so founders can focus on execution rather than figuring everything out alone.

Today those communities exist both physically and digitally.

AI communities.

Startup communities.

Founder masterminds.

Startup Club.

The entrepreneurs making the fastest progress aren’t building alone.

Visualize the Outcome Before You Build It

Before customers buy your product, they have to understand it.

Before your team builds it, they have to believe in it.

Visualization has always mattered.

AI simply gives founders better tools to communicate their vision.

Generate product mockups.

Create explainer videos.

Build clickable prototypes.

Design customer journeys.

The clearer your vision becomes, the easier it is for others to join you.

Don’t Fall in Love With Branding Too Early

Naming your company matters.

Owning the domain matters.

Protecting trademarks matters.

But don’t spend six weeks debating logos while your competitors are finding customers.

AI makes branding almost effortless.

That’s exactly why founders shouldn’t mistake branding for validation.

Customers don’t buy logos.

They buy solutions.

Investors Should Speed You Up, Not Save You

Many founders still believe funding is the first milestone.

It isn’t.

Customers are.

Before approaching investors, prove people actually want what you’re building.

Generate traction.

Build prototypes.

Earn revenue.

Collect testimonials.

AI lowers startup costs enough that many founders can validate ideas long before giving away equity.

That’s one of the biggest entrepreneurial advantages of this generation.

Sleep On It. Then Ship.

One piece of advice from the original chapter remains timeless.

Sleep on your idea.

Great entrepreneurs aren’t impulsive.

They pause.

They think.

They gather feedback.

Then they move decisively.

AI gives us instant answers.

Entrepreneurship still rewards thoughtful decisions.

Don’t confuse speed with wisdom.

Action Is Still the Ultimate Competitive Advantage

Every generation thinks entrepreneurship has fundamentally changed.

It hasn’t.

The tools change.

The principles don’t.

AI has made creating easier.

It has made testing faster.

It has lowered the cost of experimentation.

But it has not replaced courage.

It has not replaced customer conversations.

It has not replaced persistence.

And it certainly has not replaced execution.

The entrepreneurs who build the next generation of great companies won’t necessarily have the best ideas.

They’ll simply be the ones who stop waiting and start building.

Ideas are cheap.

Execution has always been the advantage. AI just makes that more obvious.

For the past decade, entrepreneurs have obsessed over finding the perfect idea. Today, AI can generate a hundred business ideas before you’ve finished your morning coffee. It can write business plans, build prototypes, design logos, and even create marketing campaigns in minutes.

None of that matters if you never ship.

This article is adapted from Chapter 2 of Colin C. Campbell’s bestselling book, Start. Scale. Exit. Repeat. While the original chapter was written before today’s AI explosion, its central lesson has become even more relevant:

Ideas don’t create companies. Action does.

The Uber That Never Happened

Years before Uber became one of the world’s most valuable startups, my partners and I found ourselves stranded in foreign cities trying to find taxis.

We imagined an app that would use GPS to locate nearby taxis, summon one instantly, and let you watch it arrive.

We even bought the domain.

Then we moved on to another project.

Someone else executed.

That’s entrepreneurship in a nutshell.

History doesn’t reward the first person who thinks of an idea. It rewards the first team that brings it to life.

Today AI makes this lesson even harsher.

If AI helped you think of an idea, chances are it helped thousands of other entrepreneurs think of it too.

The only differentiator left is execution.

AI Is Your Accelerator, Not Your Business

Many founders treat AI like the business itself.

It isn’t.

AI is simply leverage.

Use it to validate customer demand faster.

Use it to build prototypes.

Use it to write copy, analyze competitors, summarize customer interviews, or generate your first website.

But don’t confuse productivity with progress.

You can spend weeks prompting ChatGPT without talking to a single customer.

That’s still procrastination.

The entrepreneurs who win will be the ones using AI to spend more time with customers, not less.

Share Your Idea Earlier Than Ever

Many founders still worry someone will steal their idea.

That’s almost never the real risk.

The bigger risk is building something nobody wants.

One of the first actions every entrepreneur should take is sharing the idea with people who understand the space and with potential customers who might actually buy it. Their feedback improves the idea, identifies blind spots, and often introduces the partners, mentors, or investors you’ll eventually need.

AI can simulate feedback.

Real people provide reality.

Use both.

Build Before You Feel Ready

One of the biggest changes AI has created is the speed at which entrepreneurs can test assumptions.

You don’t need six months to build an MVP anymore.

You can launch a landing page today.

Generate mockups this afternoon.

Create demo videos tonight.

Collect customer feedback tomorrow.

The barrier to building has collapsed.

The barrier to acting is still entirely psychological.

Find Your Entrepreneurial Playground

One of the best ways to move from idea to execution is by surrounding yourself with builders.

Incubators, accelerators, entrepreneur communities, and startup organizations provide accountability, introductions, feedback, and practical support that dramatically increase your chances of success. They exist to remove barriers so founders can focus on execution rather than figuring everything out alone.

Today those communities exist both physically and digitally.

AI communities.

Startup communities.

Founder masterminds.

Startup Club.

The entrepreneurs making the fastest progress aren’t building alone.

Visualize the Outcome Before You Build It

Before customers buy your product, they have to understand it.

Before your team builds it, they have to believe in it.

Visualization has always mattered.

AI simply gives founders better tools to communicate their vision.

Generate product mockups.

Create explainer videos.

Build clickable prototypes.

Design customer journeys.

The clearer your vision becomes, the easier it is for others to join you.

Don’t Fall in Love With Branding Too Early

Naming your company matters.

Owning the domain matters.

Protecting trademarks matters.

But don’t spend six weeks debating logos while your competitors are finding customers.

AI makes branding almost effortless.

That’s exactly why founders shouldn’t mistake branding for validation.

Customers don’t buy logos.

They buy solutions.

Investors Should Speed You Up, Not Save You

Many founders still believe funding is the first milestone.

It isn’t.

Customers are.

Before approaching investors, prove people actually want what you’re building.

Generate traction.

Build prototypes.

Earn revenue.

Collect testimonials.

AI lowers startup costs enough that many founders can validate ideas long before giving away equity.

That’s one of the biggest entrepreneurial advantages of this generation.

Sleep On It. Then Ship.

One piece of advice from the original chapter remains timeless.

Sleep on your idea.

Great entrepreneurs aren’t impulsive.

They pause.

They think.

They gather feedback.

Then they move decisively.

AI gives us instant answers.

Entrepreneurship still rewards thoughtful decisions.

Don’t confuse speed with wisdom.

Action Is Still the Ultimate Competitive Advantage

Every generation thinks entrepreneurship has fundamentally changed.

It hasn’t.

The tools change.

The principles don’t.

AI has made creating easier.

It has made testing faster.

It has lowered the cost of experimentation.

But it has not replaced courage.

It has not replaced customer conversations.

It has not replaced persistence.

And it certainly has not replaced execution.

The entrepreneurs who build the next generation of great companies won’t necessarily have the best ideas.

They’ll simply be the ones who stop waiting and start building.

Ideas Are Everywhere: How Great Businesses Start by Solving Everyday Problems

The best business ideas don’t begin in a brainstorm. They begin with an annoyance.

Entrepreneurs love talking about “the next big idea.” They chase trends, study markets, and wait for inspiration to strike. But in reality, the strongest companies rarely start with a revolutionary invention. They start with someone noticing something that shouldn’t be that way.

That’s how almost every successful entrepreneur I know got started.

Your Frustration Is Trying to Tell You Something

For years, I spent more nights in hotels than I care to remember.

Hotels offered comfortable beds, consistent quality, and professional service. Vacation rentals offered space, kitchens, and a more authentic travel experience. The problem was that you had to choose one or the other.

Vacation rentals often came with uncomfortable mattresses, worn-out furniture, and cookware that had clearly seen better days. It always felt like property owners assumed guests wouldn’t care.

I cared.

That frustration eventually became Escape Club, our vacation rental business built around one simple idea: combine the comfort and consistency of a premium hotel with the freedom of a vacation rental.

Luxury beds. High-quality cookware. Better design. Better experience.

It wasn’t a breakthrough technology. It was simply solving a problem that many travelers already had.

That’s where ideas begin.

Start With Why, Not With Money

Too many entrepreneurs begin with the wrong question.

Instead of asking, “What problem can I solve?” they ask, “How can I make money?”

The difference matters.

Startups are difficult. Every business hits obstacles. If your only motivation is getting rich, the first setback will probably convince you to quit.

Purpose keeps you moving when profits haven’t arrived yet.

Your “why” doesn’t have to change the world. It simply has to matter to you.

Maybe you want families to have better vacations. Maybe you want to make healthcare easier. Maybe you want to eliminate a frustrating daily task.

If you genuinely care about improving someone’s life, you’re already starting from a much stronger foundation.

Opportunities Reward People Who Pay Attention

One day my son found a twenty-dollar bill on the ground.

He thought he was lucky.

I told him he was observant.

Entrepreneurship works the same way.

Business opportunities rarely arrive with flashing lights announcing themselves. They’re usually hiding inside everyday inconveniences, conversations, complaints, and trends.

The entrepreneurs who consistently discover great ideas aren’t necessarily more creative than everyone else.

They’re simply paying closer attention.

Train yourself to notice what others ignore.

When an idea comes, don’t trust yourself to remember it later.

Write it down.

Build a simple business plan around it.

Talk to people you trust enough to give honest feedback—not people who automatically tell you every idea is brilliant, and not those who shoot everything down before you’ve even started.

Every Problem Is an Opportunity Wearing Different Clothes

Many of the best businesses begin with personal frustration.

Startup Club member Marcia Reece watched her daughter drawing with toxic chalk and decided children deserved something better.

She created colorful, non-toxic sidewalk chalk.

She tested it at craft fairs, learned what customers wanted, refined the product, and eventually landed in Walmart.

The idea wasn’t complicated.

The observation was.

The same pattern repeats itself over and over.

Someone experiences wrist pain from computer keyboards and creates ergonomic wrist supports.

Someone struggles with food going bad and develops technology to keep produce fresh longer.

Someone watches a loved one struggle with incontinence and builds a product that restores confidence and dignity.

The common thread isn’t genius.

It’s empathy.

The best entrepreneurs don’t ignore problems.

They become obsessed with solving them.

Not Every Good Idea Is a Great Business

Having a clever idea isn’t enough.

Before investing your time and money, ask yourself three simple questions:

  • Does it solve a real problem?
  • Can enough people benefit from it for the business to grow?
  • Can you build something competitors can’t immediately copy?

If the answer is no to any of those questions, keep refining.

Ideas deserve testing before they deserve funding.

Fall in Love With the Problem

People often say you should fall in love with your product.

I think it’s even more important to fall in love with the problem you’re solving.

Businesses evolve.

Markets change.

Technology advances.

But if you’re committed to solving an important problem, you’ll continue adapting until you find the right solution.

Years ago, my brother Bill and I operated one of Canada’s largest bulletin board systems.

It was successful.

It generated cash flow.

Then we started hearing about something called the internet.

We realized we couldn’t fully pursue both businesses.

So we shut down the company that was working in order to build the one we believed represented the future.

That decision led to Internet Direct, which eventually became Canada’s largest internet service provider.

Sometimes your next opportunity requires letting go of yesterday’s success.

Your Current Job Might Be Your Next Startup

Many entrepreneurs assume they need to invent something completely new.

Most don’t.

Some of the best businesses simply improve an existing process.

Others emerge directly from experience inside an industry.

One conversation with a telecommunications company led us to realize there was demand for private-label web hosting platforms.

That insight became Hostopia, a company that still powers some of the world’s largest telecom providers today.

You don’t need a lightning bolt.

You need awareness.

Listen carefully inside your industry.

Notice bottlenecks.

Pay attention to customer complaints.

Observe inefficient systems.

Your next business might already be sitting in front of you.

The Twenty-Dollar Bill Is There

Ideas are everywhere.

Most people simply walk past them.

The entrepreneurs who consistently build businesses aren’t luckier than everyone else. They train themselves to see opportunities hiding inside everyday experiences.

Every complaint is a clue.

Every frustration is feedback.

Every inconvenience is a question waiting for someone to answer.

The next great business isn’t waiting for inspiration.

It’s waiting for someone observant enough to notice it.

Check out Start. Scale. Exit. Repeat. on Amazon for more!

Launching a Top-Level Domain: Colin C. Campbell on Building .Club

Most people see a domain extension like .club and assume the hard part is getting approved.

It’s not.

On the latest episode of the Domain Name Wire Podcast hosted by Andrew Allemann, Colin C. Campbell shares what it actually takes to build a successful top-level domain, drawing on his experience launching .Club, growing it into one of the world’s largest new domain extensions, and ultimately selling the business to GoDaddy.

Getting a TLD delegated is just the beginning. The real challenge is building adoption. Colin discusses how long it took .Club to become profitable, why distribution partnerships with registrars are critical, and why success requires patience, capital, and long-term execution. Unlike a typical startup launch, a domain extension is infrastructure. Growth happens over years, not months.

With the ICANN application window closing on August 12, Colin also explains why he’s returning to the market and applying again. Despite the challenges, he believes there are still meaningful opportunities for entrepreneurs who understand the industry, have a clear strategy, and are prepared to play the long game.

Whether you’re considering applying for a new top-level domain or you’re simply interested in how internet infrastructure businesses are built, this conversation offers an honest look behind the curtain. It’s a practical discussion about entrepreneurship, distribution, persistence, and creating long-term value in one of the internet’s most unique markets.

Check out the full conversation above, or stream the podcast!

Open Mic: AI Agents for Startups

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Open Mic: AI Agents for Startups

https://www.clubhouse.com/i/open-mic-ai-agents-for-startups/LWGCB5Dc

10 AI Agents Every Entrepreneur Needs – Serial Entrepreneur

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10 AI Agents Every Entrepreneur Needs – Serial Entrepreneur

https://www.clubhouse.com/i/10-ai-agents-every-entrepreneur-needs-serial-entrepreneur/sZ3vO41d