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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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Uncontrollable Forces, Unforeseen Business Challenges

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Uncontrollable Forces, Unforeseen Business Challenges

What happens when the economy crashes, interest surges, or tariffs strike? Every business faces external forces – how can yours adapt and survive?

https://www.clubhouse.com/i/uncontrollable-forces-unforeseen-business-challenges/g5C8lvo5

Uncontrollable Forces, Unforeseen Business Challenges

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Uncontrollable Forces, Unforeseen Business Challenges

What happens when the economy crashes, interest surges, or tariffs strike? Every business faces external forces – how can yours adapt and survive?

https://www.clubhouse.com/i/uncontrollable-forces-unforeseen-business-challenges/g5C8lvo5

EP214: AI Agents Are Not Magic. They’re the New Workforce for Entrepreneurs

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AI Agents: The Next Evolution for Entrepreneurs

AI is shifting from simple prompts to powerful, task-driven agents—and entrepreneurs who understand this shift will have a major edge. In this episode of Start Scale Exit Repeat, Steve Simonson joins Colin C. Campbell and Michelle Van Tilborg to break down how founders can use AI practically, starting small and focusing on point-to-point solutions. The takeaway: treat AI like a team of interns, not a magic replacement, and build smarter, faster workflows with the right oversight.

AI Agents Are Not Magic. They’re the New Workforce for Entrepreneurs

Artificial intelligence is no longer just about asking ChatGPT a question and getting an answer. The next wave is already here, and for entrepreneurs, it may become one of the most important shifts in how businesses scale.

On Start Scale Exit Repeat: Serial Entrepreneur Secrets Revealed, entrepreneur and e-commerce veteran Steve Simonson joined Colin C. Campbell and Michelle Van Tilborg to break down the rapidly evolving world of AI agents and what founders actually need to understand right now.

The discussion cut through much of the hype surrounding AI. Simonson, who has been building AI-driven workflows for years, offered a simple but powerful definition: AI agents are tools designed to complete a specific task from point A to point B.

“Think about AI first as your solution,” he said. “Can AI actually handle this task? Not job. Task.”

“Most agents are trained on a specific set of data and have what I call a point-to-point trajectory,” Simonson explained. “There’s some input or trigger that causes them to interact with their knowledge base, and then they produce some sort of predictable output.”

In other words, entrepreneurs should stop imagining one giant super-AI running an entire company and instead think about AI as a growing team of specialized assistants.

Simonson compared many of today’s AI agents to interns. They are capable, productive and increasingly powerful, but they still require management, oversight and clear direction.

“You’re the manager,” he said. “It’s the intern.”

That distinction matters because many founders are currently overwhelmed by AI. Michele admitted she feels anxiety about moving too slowly and missing the opportunity entirely. Steve’s advice was refreshingly practical: slow down, stay calm and start small.

“Think about AI first as your solution,” he said. “Can AI actually handle this task? Not job. Task.”

That difference became one of the most valuable lessons from the conversation. Entrepreneurs should not try to automate an entire company overnight. Instead, they should isolate one repetitive function and solve that first.

A roofing company, for example, might use an AI voice bot to answer incoming calls, schedule appointments and handle simple customer questions while the owner is physically on a roof working. A media company could use AI to chop podcasts into social clips. A founder selling tea internationally could use AI tools to research foreign markets, competitors and market entry strategies.

The common thread is focus.

“Point-to-point wins,” Steve repeated throughout the discussion.

The panel also explored the growing ecosystem of AI tools available to entrepreneurs. Steve recommended no-code platforms that allow founders to build simple bots without engineering expertise. He pointed to tools like Manus, which can create presentations, websites, research reports and marketing assets in minutes.

Colin shared his own experience using AI to build an app despite having no software development background. After dozens of iterations, screenshots and corrections with Claude AI, he successfully got the app running in just a few hours.

The process was messy, but it proved an important point: founders no longer need to be programmers to create technology.

“We’re truly only limited by our imagination now,” Colin C. Campbell said.

Still, the conversation did not ignore the risks. Participants warned against blindly handing over sensitive systems like banking or accounting to autonomous AI agents. Human oversight remains essential.

“Garbage in, garbage out,” Steve Simonson cautioned.

Several speakers emphasized the importance of business rules, approvals and guardrails. AI can accelerate execution, but entrepreneurs still need strategy, judgment and accountability.

The most interesting takeaway may have been philosophical rather than technical. Steve urged entrepreneurs to adopt a mindset of constant learning and humility, even after years of success.

“I don’t know nothing about nothing,” read the slogan on his T-shirt during a recent conference appearance.

For founders navigating the AI era, that attitude may be the real competitive advantage. The technology is evolving too quickly for anyone to pretend they already have all the answers.

What matters now is curiosity, adaptability and the willingness to experiment.

The entrepreneurs who embrace that mindset today may build the companies that define the next decade.

EP213: Work Hard, Play Hard: The Entrepreneur’s Balancing Act

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Designing a Balanced Entrepreneurial Life

Entrepreneurship isn’t just about relentless hustle. It’s also about building a life that can sustain that ambition. In this episode of The Complete Entrepreneur, Colin C. Campbell and Michael Gilmour explore how founders can align work, family, and personal rewards without burning out. From treating business like a game to celebrating small wins, this conversation reframes what it really means to succeed as an entrepreneur.

Hosts: Colin C. Campbell, Michael Gilmour

Work Hard, Play Hard: The Entrepreneur’s Balancing Act

Entrepreneurs are often told to work hard. Less often are they reminded to play hard, not as an escape from the work, but as part of the life they are trying to build.

On The Complete Entrepreneur, hosts Colin C. Campbell and Michael Gilmour explored that tension in a conversation about energy, ambition, family, rewards and the strange reality that, for many entrepreneurs, work does not always feel like work.

“Nothing existed without the work of an entrepreneur”

“For me, I view my business as basically an amazing game,” Gilmour said. “There’s no computer game in the world like my business.”

That idea became one of the central themes of the discussion. Entrepreneurship is not a tidy nine-to-five existence. It often spills into evenings, weekends and vacations. Campbell noted that when a major deal is on the table, “there is no such thing as evenings and weekends.” The work must get done.

But the question is not simply whether entrepreneurs should work hard. They already do. The deeper question is how they can build a life that does not collapse under the weight of their ambition.

Gilmour argued that entrepreneurs are, by nature, unbalanced people. They are the “tip of the spear,” the ones pushing society forward by creating new products, new companies and new possibilities. “Nothing existed without the work of an entrepreneur,” he said. “Someone, some entrepreneur somewhere said, I think I can build a better world.”

Campbell pushed back slightly, not against the intensity itself, but against letting it consume everything. He described entrepreneurship as more organic than balanced. He may work late at night on a new venture, then spend the middle of a weekday playing cards with family. That flexibility is one of the gifts of entrepreneurship, but it also requires rituals that signal when work is over.

For Campbell, that ritual might be the hot tub. For Gilmour, it was once putting on moccasins at home, a signal to his family that “Dad’s at home.” These small transitions matter because entrepreneurs rarely switch off naturally.

Guest Jason Kinte added another important layer: life stage matters. A young founder may be able to work around the clock with few responsibilities. But someone trying to build a family may want more stability, more structure and the ability to go on a date or honeymoon without worrying whether a deal has closed.

That does not mean ambition disappears. It means the business must fit the season of life.

One of the strongest ideas from the conversation was that entrepreneurs should design their companies around the life they want. Gilmour chose to build a work-from-home business when his children were young. Campbell has leaned into ventures connected to his passions, including dogs and life at sea. Kinte spoke about wanting control rather than being driven by investors.

The point is not to avoid hard work. It is to make sure the work serves a larger purpose.

Celebration was another recurring theme. Campbell warned younger entrepreneurs against waiting too long to enjoy the journey. Do not wait for the final exit, the huge valuation or the perfect moment. Celebrate the first distributor, the first product launch, the first meaningful win.

Gilmour agreed, admitting that he often struggles with this himself. “You have to reward yourself as an entrepreneur,” he said. Rewards can be large, like a long-awaited trip or conference, or small, like great seats at a show, a family outing or even paying for a stranger’s groceries after a good week.

In the end, “work hard, play hard” is not about reckless hustle followed by reckless indulgence. It is about building a life where work, creativity, family, rest and reward are not enemies.

For entrepreneurs, the work may always be intense. The challenge is to make sure the life around it is rich enough to be worth the effort.

What to Do When Disaster Strikes – Complete Entrepreneur

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What to Do When Disaster Strikes – Complete Entrepreneur

https://www.clubhouse.com/invite/QK7fKX3dzEjVq6e6eWVNaop6l88BCDq7WXX:mohuXBs6q7zQYvcVOwCuzjtiByQOjXDVJPThE5He6is

Strategizing & Networking in the age of AI

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Strategizing & Networking in the age of AI

Speaking with George Dubec- author and coach about business networking & using AI to scale

https://www.clubhouse.com/invite/gg1SwDEZ1NlLgZGXQ8AQV3Y9ddWzUnpLXYY:OcEMG3PRzNdYg5LpPbtSf8OOrh_xlP2IjFF0Grigu60

It’s Time America Launches .USA Domain

Why .USA Is the National Domain America Actually Needs

I have spent over thirty years building things on the internet. I helped found CIRA, the Canadian Internet Registration Authority, the organization that runs .CA. We built .CLUB from nothing and ran it for nine years before selling it to GoDaddy. I know what it takes to build a domain that means something to people.

And every time I look at .US, I feel a sense of loss.

Not anger. Loss.

Because America deserves so much better.

Every four years, the Olympics come around. Athletes from every nation walk into the opening ceremony wearing their country’s identity on their chest. Not their state. Not their region. Their country.

Canada wears CAN. Germany wears GER. Japan wears JPN.

And the United States walks in wearing USA.

Three letters. Proud. Unmistakable. The whole world knows exactly what it means.

So why, when an American business goes online, do they have to settle for .US?

“US” is a pronoun. It means nothing. It evokes nothing. It is the digital equivalent of walking into the Olympics with a name tag that says “us.”

When I was helping build .CA in Canada, we understood something important. The domain was not just a technical address. It was a statement. It said: this is Canadian. This came from here. You can trust this.

That is what a national domain should do.

Germany understood this. .DE has over 17 million registrations. The Netherlands understood it. .NL has more registrations per capita than almost any country on earth. Canada understood it. .CA has more registrations per capita than the United States by a factor of thirteen.

The most powerful nation on earth has one of the weakest national domains in the world.

That is a policy failure. Not a public failure. The American people never rejected .US. They were never really given a reason to embrace it.

What I believe in is .USA.

Not as a technical experiment. Not as a policy paper. As a national trust mark.

Imagine a domain reserved only for companies and products that are genuinely, verifiably American. Where buying from a .USA website means something. Where a manufacturer in Ohio or a craftsman in Tennessee or a software company in Texas can put .USA after their name and have it mean exactly what it sounds like.

That is what .USA can be.

It is the digital version of “Made in USA” on the label. It is the online equivalent of that Olympic uniform. It is a signal the whole world understands.

I have been asked what happens if we cannot get .USA approved through ICANN. It is a fair question. The process is long and there are no guarantees.

What if we can’t get .USA: then lets reboot .US.

We take what exists, strip away the bureaucracy, and build it into something Americans actually want to use. We market it the way .CA was marketed in Canada. We give businesses a reason to choose it. We make it mean something.

Because the worst outcome is doing nothing.

The United States cannot be the country that leads the world in technology and innovation while also being the country that cannot figure out how to make its own national domain relevant.

I am not a politician. I am not a lobbyist. I am an entrepreneur who has spent his career building things that matter.

And I believe .USA matters.

Not because of the business opportunity. Because of what it represents.

Every country deserves a digital identity it can be proud of. Every nation should be able to say: here is where we are. Here is what we stand for. Here is our mark on the internet.

America has that chance.

It is called .USA.

And it is long overdue.

EP212: What Private Equity Isn’t Telling You Before You Sign with Alexis Sikorsky

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What founders get wrong about selling… and how to exit with leverage

In this episode, Colin C. Campbell and Michele Van Tilborg are joined by Alexis Sikorsky to break down what founders misunderstand about selling their business—and how to maximize value when exiting. Drawing from his experience on both sides of the deal, Alexis shares how to position your company for private equity, prepare years in advance, and avoid costly mistakes that leave money on the table. If you’re thinking about an exit, this is a practical guide to navigating the process with clarity and control.

Hosts: Colin C. Campbell, Michele Van Tilborg

Guest: Alexis Sikorsky

More info about Alexis, plus the link to order his book ‘Cashing Out’ here: https://www.asikorsky.com/