Home Blog

EP36: What Actually Works when Raising Money

0

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

Sign up to our email and never miss an update on our special events, guest speakers, and more: https://startup.club/

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

0

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

0

10 AI Agents Every Entrepreneur Needs – Serial Entrepreneur

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

10 AI Agents Every Entrepreneur Needs – Serial Entrepreneur

0

10 AI Agents Every Entrepreneur Needs – Serial Entrepreneur

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

Real Estate, Leadership & Growth – Serial Entrepreneur: Secrets Revealed

0

Real Estate, Leadership & Growth – Serial Entrepreneur 

Speaking with Adam Stein, Real Estate Broker & Performance Coach about scaling, leading, and winning at a high level.

ROOM LINK: https://www.clubhouse.com/i/real-estate-leadership-growth-serial-entrepreneur/slDKLRrV

EP222: The Entrepreneur’s Roller Coaster: How to Stay Steady Through the Highs and Lows

Entrepreneurship is rarely a smooth ride. One day can bring momentum, validation, and growth; the next can bring rejection, financial pressure, or a problem that threatens to derail everything. In this conversation, Colin C. Campbell and Michael Gilmore explore the emotional reality of building a business through the lens of “the entrepreneur’s roller coaster.”

The discussion covers how founders can better manage the shocks that come with running a company, from broken deals and changing market conditions to team pressure, family stress, and personal burnout. Michael shares practical ways he protects his mental clarity, including setting firm weekend boundaries, taking periodic solo planning retreats, and finding trusted people outside the family to serve as a pressure-release valve.

How Entrepreneurs Can Catch the Next Tech Wave

Every major technology wave looks obvious in hindsight. The internet. Broadband. Cloud computing. Smartphones. The sharing economy. Artificial intelligence.

But in the beginning, none of them looked inevitable. They looked strange, experimental, expensive, impractical, or overhyped. The entrepreneurs who benefited most were not always the inventors of the technology. More often, they were the people who recognized the shift early, understood how it would change behavior, and built a focused business around the opportunity.

Catching the next tech wave is not guesswork. It requires pattern recognition, discipline, and a willingness to live close enough to the future to notice what others are missing.

Start by Living in the Future

One of the clearest ways to spot a technology wave is to use emerging tools before they become mainstream.

That does not mean buying every gadget or chasing every trend. It means deliberately surrounding yourself with the technologies that may change how people work, communicate, buy, travel, learn, or create.

Entrepreneurs who used fast internet early could see streaming, video conferencing, and online services becoming normal before the broader market did. People who experimented with Airbnb early could imagine a world where unused homes became income-producing assets. Those using AI tools every day are more likely to see practical business opportunities than people still treating AI as a novelty.

The point is simple: you cannot understand a wave from the shore. You have to get in the water.

Look for Noise, But Do Not Confuse Noise With Proof

When a new technology begins to matter, it creates noise. People talk about it in niche communities, social platforms, forums, founder groups, investor circles, and industry conversations.

That noise can be an early signal. Reddit, Clubhouse, domain marketplaces, developer communities, search trends, and keyword activity can all reveal where attention is moving before the mainstream catches on.

But noise alone is not enough. Many technologies generate attention and still fail to cross into mass adoption. NFTs, the metaverse, and certain robotics categories have all attracted massive interest while struggling to prove lasting mainstream utility.

The question is not, “Are people talking about it?” The better question is, “Are people changing their behavior because of it?”

Focus on Real Problems and Massive Opportunities

A technology wave becomes powerful when it either solves a painful problem or creates a large new opportunity.

The internet solved distribution. Broadband unlocked video, remote work, streaming, and real-time digital experiences. Airbnb unlocked underused housing supply. Starlink is opening new possibilities for remote work, maritime living, and internet access in places that were previously disconnected.

AI is doing something similar across knowledge work. It can reduce the cost of legal drafts, software development, marketing analysis, content creation, research, and business planning. That does not mean human judgment disappears. It means the economics of many services are changing.

The strongest opportunities often appear where a new technology changes the cost structure of an old problem.

Watch Your Own Behavior

A useful test for any emerging technology is whether it changes your own habits.

Do you find yourself using it repeatedly? Does it save time? Does it make something possible that previously felt too expensive, too technical, or too slow? Does it change how you think about a market?

If a tool changes your behavior, it may change the behavior of others. That does not guarantee a startup opportunity, but it is a stronger signal than hype alone.

This is especially important for founders. If you personally do not understand why a technology matters, it is risky to build around it just because investors, media, or competitors are excited. The best opportunities often begin with a clear personal insight: “I get this. I can see where it is going.”

Look for Second-Order Opportunities

The biggest businesses are not always built directly on the first wave. Many are built on the aftereffects.

Amazon began with books, then expanded into nearly everything. Facebook emerged years after the internet itself became mainstream. Airbnb was not just a website; it was a second-order opportunity created by internet trust, online payments, mobile access, and changing travel habits.

The same pattern is happening with AI. The first wave was large language models. The aftershocks include AI agents, video generation, music generation, AI-assisted legal work, AI-powered software development, internal workflow automation, and niche tools for specific industries.

Founders should look beyond the headline technology and ask what new markets become possible because of it.

Be Careful: Real Waves Can Still Create Bubbles

A technology can be useful and overhyped at the same time.

That distinction matters. The dot-com crash did not mean the internet was fake. It meant many companies had weak models, bad timing, or unsustainable valuations. The same can happen with AI, robotics, crypto, spatial computing, or any other emerging sector.

Entrepreneurs need optimism, but not blind optimism. The right approach is to test whether a technology solves a real problem, whether customers will pay, and whether the timing is right.

Some companies survive the chasm by narrowing their focus. Instead of trying to serve everyone, they become excellent in one niche. That “laser beam” approach creates survival, credibility, and expertise. Once the market matures, expansion becomes easier.

The Next Wave Is Already Forming

The next tech wave rarely announces itself clearly. It starts as experiments, conversations, niche adoption, and small behavior changes. Then, almost suddenly, it becomes obvious.

Entrepreneurs do not need to invent the next foundational technology to benefit from it. They need to recognize the shift, find the practical use case, focus on a specific market, and move before everyone else understands the opportunity.

The formula is not perfect, but it is repeatable: live near the future, listen for signal, test for real behavior change, solve a meaningful problem, watch for second-order effects, and stay disciplined enough to avoid hype.

The next wave is already out there. The advantage goes to the people paying attention before it becomes common knowledge.

The Entrepreneur’s Roller Coaster: How to Stay Steady Through the Highs and Lows

Entrepreneurship is often described in heroic language: freedom, vision, independence, impact. All of that can be true. But anyone who has built a company knows the other side of the story. The same business that gives you energy in the morning can leave you exhausted by the afternoon. A single phone call can change the mood of an entire week. A strong sales month can make you feel unstoppable. A failed deal can make you question every decision that led you there.

That is the entrepreneur’s roller coaster. It is not a metaphor reserved for dramatic startups or venture-backed founders. It is the daily emotional rhythm of owning responsibility when there is no safety net beneath you.

The goal is not to eliminate the ride. That is impossible. The goal is to learn how to stay steady while the ride continues.

The Lows Are Real, but They Are Rarely Final

Every founder eventually gets hit with bad news. A lender pulls back. A broker passes. A customer leaves. A supplier raises prices. A deal changes shape. A new regulation, tax change, tariff, or market shift appears at exactly the wrong time.

In the moment, these events can feel catastrophic. The mind tends to take a single setback and turn it into a full collapse. But most business problems are not final verdicts. They are problems to be worked.

That distinction matters.

When founders freeze, avoid the issue, or spiral emotionally, the problem usually gets worse. When they move into action, even imperfect action, they regain some control. Calling a strategic planning session, bringing in trusted advisors, reviewing costs, reworking a sales strategy, or simply writing down the next three decisions can create momentum. Progress does not always solve the problem immediately, but it changes the founder’s relationship to the problem.

Doing something is almost always better than sitting inside the panic.

Founders Need a Pressure-Release Valve

One of the hardest parts of entrepreneurship is that founders often carry stress they cannot fully share with their teams, families, or partners. They are expected to be the calming force while privately absorbing the uncertainty.

That pressure has to go somewhere.

Every entrepreneur needs someone they can speak to honestly. Not someone to dump on endlessly, and not necessarily a spouse or family member, but someone who understands the weight of business ownership and can hear the truth without becoming destabilized by it.

Family members can be supportive, but they are often emotionally tied to the outcome without having any control over it. Sharing only the bad news at home can unintentionally make them passengers on a roller coaster they did not choose and cannot steer. A spouse, partner, or child may hear the problems but never hear the resolutions, victories, or context. Over time, that can strain relationships.

A trusted peer group, mentor, advisor, or fellow entrepreneur can help absorb the emotional load in a healthier way. Founders need spaces where they can be blunt, uncertain, frustrated, and honest without turning their households into boardrooms.

Boundaries Are Not Optional

The nonstop nature of entrepreneurship makes boundaries feel unrealistic. There is always another email, problem, deal, invoice, decision, or fire to put out. But founders who never step away eventually lose the clarity required to lead.

A firm weekend boundary can be one of the simplest stabilizers. Not every founder can fully avoid weekend work, especially during a crisis, but creating a default rhythm of disconnection gives the mind and body a chance to reset. It also signals to family and team members that the business does not own every hour of life.

Some founders also benefit from periodic solo planning retreats. Taking a day or two away from the normal environment can create enough distance to think clearly. The first step may simply be unloading every stress, concern, and fear into a private document. Once the noise is out of the founder’s head, it becomes easier to shift from anxiety to strategy.

That is where better questions emerge: What is actually happening? What are the strengths, weaknesses, opportunities, and threats? What decisions need to be made? What action items matter most when returning to the business?

Clarity rarely appears in the middle of constant interruption. Sometimes it has to be created deliberately.

Success Can Be Just as Dangerous as Failure

The lows of entrepreneurship are obvious. The highs are more deceptive.

Success can create arrogance. Revenue growth, investor attention, strong press, or a rising valuation can convince founders they are smarter than they are. They begin to overspend, overhire, ignore warning signs, or assume the current momentum will last forever.

That is where the top of the roller coaster becomes dangerous.

A strong period in business should create discipline, not ego. When things are going well, founders should be asking how to protect the company, reward the team, build cash reserves, and prepare for the next downturn. Growth matters, but growth without restraint can become gambling.

There is a difference between leaning into momentum and spending every dollar as if the future is guaranteed. A business with cash reserves has options. It can hire when others are cutting, launch when competitors are stalled, or survive when the market turns. A business that spends everything during the good times has no cushion when the ride drops.

Calm Is a Leadership Skill

Teams often take their emotional cues from the founder. If the founder panics, the team panics. If the founder becomes arrogant, the team absorbs that too. If the founder stays calm, focused, and direct, the company has a better chance of working through the issue.

“Let’s work the problem” is one of the most useful mindsets a founder can bring into a crisis. It does not deny the seriousness of the situation. It simply refuses to let emotion become the operating system.

The entrepreneur’s roller coaster is unavoidable. There will be highs. There will be lows. There will be days that feel exhilarating and days that feel punishing. The founders who last are not the ones who avoid those extremes. They are the ones who learn how to respond with discipline, humility, and perspective.

In the end, entrepreneurship is not only a test of business skill. It is a test of character. It reveals how a person handles pressure, success, uncertainty, relationships, and responsibility. The ride may never flatten completely, but with the right habits and support systems, founders can stay steady enough to keep building.

EP221: AI Growth Hacks Every Entrepreneur Should Be Using Now

In this episode of Serial Entrepreneur Secrets Revealed, the Startup Club community dives into practical AI growth hacks entrepreneurs are using right now to start, scale, and streamline their businesses.

The conversation covers real-world examples across legal documents, marketing analytics, inventory management, inbox prioritization, co-living operations, bookkeeping, content creation, workshops, and AI agents. One founder shares how AI helped draft a private placement memorandum in hours instead of requiring thousands of dollars in upfront legal costs. Another explains how ChatGPT was used to photograph furnished rental units, estimate replacement values, and generate an inventory spreadsheet. Others discuss using AI for inbox triage, customer lifetime value analysis, Facebook “Buy Nothing” sourcing, agent workflows, and NotebookLM-powered research.