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/

What Happens when AI Agents can Replace Your Staff?

0

What Happens when AI Agents can Replace Your Staff?

https://www.clubhouse.com/i/what-happens-when-ai-agents-can-replace-your-staff/FVoWXgSQ

EP219: What To Do When Disaster Strikes: The Entrepreneur’s Real Test

0

The Real Measure Of An Entrepreneur is How they Lead When Things Go Wrong

In this episode of The Complete Entrepreneur, Colin C. Campbell and Michael Gilmour tackle a topic most founders avoid until it is staring them in the face: disaster.

From losing venture capital overnight to watching companies collapse during the dot-com crash, they share raw stories about business failures, external shocks, financial devastation, and the emotional toll of entrepreneurship.

More importantly, they explore what separates entrepreneurs who recover from those who don’t.

  • Why integrity matters most when everything is falling apart
  • How transparency can turn a crisis into an opportunity
  • The emotional reality of entrepreneurial disasters
  • What founders learn when they lose everything
  • Why entrepreneurship is ultimately a skill, not a single outcome
  • How to make decisions from facts instead of emotion during a crisis

What To Do When Disaster Strikes: The Entrepreneur’s Real Test

The Day Everything Breaks Is The Day Leadership Begins

Most entrepreneurs don’t fail when disaster strikes. They fail in the days that follow.

Nobody teaches you what to do when your investor disappears.

Nobody teaches you what to do when a key customer leaves.

Nobody teaches you what to do when the company you’ve spent ten years building suddenly starts collapsing around you.

The startup world loves victory stories. Funding announcements. Exits. Unicorn valuations.

What rarely gets discussed are the nights when founders stare at the ceiling wondering how they’ll make payroll next week.

Those moments are the real test.

This article is based on a conversation with Colin C. Campbell and Michael Gilmour on handling entrepreneurial disasters.

“When everything else disappears, integrity is the one asset you cannot afford to lose.”

Transparency Beats Panic

One of the most powerful stories came from a crisis that should have destroyed a business.

A utility company accidentally severed hundreds of critical phone lines serving a major internet provider. Overnight, thousands of customers lost service.

The easy response would have been silence. The actual response was the opposite.

The company immediately issued a press release, explained exactly what happened, and faced the problem publicly.

What looked like a catastrophe became national news.

The business recovered. The brand became stronger.

When disaster hits, people usually forgive bad news. They rarely forgive being misled.

Transparency creates trust when trust matters most.

Integrity Is Your Last Remaining Asset

Michael Gilmour shared a story every founder should hear.

After raising millions in venture capital, his company hit every milestone. Then an acquisition between two global corporations wiped out future funding commitments overnight.

The business was suddenly fighting for survival.

Employees had to be informed. Investors had to be informed. Creditors had to be informed. None of those conversations were easy.

Yet years later, many of those same investors backed him again.

Why?

Not because the company succeeded.

Because the founder operated with integrity when things failed.

Founders often think leadership is about vision.

During a crisis, leadership becomes character.

The Loneliest Job In Business

Entrepreneurship can be incredibly rewarding. It can also be incredibly lonely.

When disaster strikes, founders often discover something uncomfortable.

Most people around them cannot truly understand what they’re carrying.

Employees worry about their jobs. Investors worry about their money. Customers worry about service.

The founder worries about all of it. At the same time. That weight is difficult to explain unless you’ve carried it yourself.

The reality is simple. Leadership often means absorbing uncertainty so others don’t have to.

Facts First. Emotions Second.

Every entrepreneur experiences emotional reactions.

Anger. Fear. Frustration. Panic.

Those emotions are normal.

What matters is what comes next.

When faced with major external shocks, successful founders gather facts before making decisions.

Not assumptions. Not headlines. Not social media opinions. Facts.

One practical lesson from the conversation stood out.

Before making a major decision, build the spreadsheet. Map the options. Calculate the outcomes. Evaluate reality instead of reacting to emotion.

The crisis may not change.

Your response can.

Every Disaster Is An Expensive Training Course

Colin shared the story of losing over $100 million during the dot-com collapse.

It was devastating. Years of work evaporated. Employees lost jobs. Investors lost money.

A dream disappeared.

Yet that experience became the foundation for future success, including multiple successful exits and eventually the bestselling book Start. Scale. Exit. Repeat.

The lesson wasn’t financial. It was operational.

Every disaster teaches something.

Sometimes the tuition is painfully expensive.

The founders who survive are the ones who pay attention to the lesson.

Entrepreneurs Know How To Start Again

This may be the most important insight of all.

Entrepreneurship is not a single company.

It’s not a funding round. It’s not an exit. It’s a skill.

A founder who has learned how to create value can do it again. And again. And again.

Companies come and go.

Markets rise and fall.

Technology changes.

The skill remains.

That’s why experienced investors often back entrepreneurs who have failed before.

Not despite the failure. Because of it.

The Real Measure Of An Entrepreneur

Rocky Balboa said it best.

“It ain’t about how hard you hit. It’s about how hard you can get hit and keep moving forward.”

Every entrepreneur gets hit.

The question is never whether disaster will arrive.

The question is what you’ll do when it does.

Because in business, as in life, resilience is not avoiding the storm.

It’s learning how to build again after it passes.

5 Ways To Improve Customer Experience Without Adding Headcount

Customer satisfaction is the foundation of any successful business, but scaling customer experience (CX) often requires costs and personnel that new businesses cannot afford. However, there are certain methods through which any brand can boost its CX without adding a single person. In this article, we discuss five key ways to improve customer experience without adding headcount.

1. Knowledge Bases

Knowledge bases are one of the most efficient and cost-effective ways to help your customers resolve their own issues. To start out, you can add FAQs to your website that answer the most common questions that customers have about your brand’s products or services. Add a few of them to each landing page, or make a dedicated webpage for FAQs and their answers.

Once you’re set up with FAQs, you can build a full knowledge base of articles that will educate customers on various topics related to your brand. Instead of providing the kind of succinct answers expected in FAQ answers, these articles should comprehensively cover topics or subtopics. For example, you could have a page that explains how to set up a particular device you sell while another page explains basic troubleshooting exercises for that device.

2. AI Assistants

Thanks to technological advancements, AI assistants are becoming an increasingly popular way to resolve basic customer issues. They can be implemented as a basic level of customer service before you can hire more staff, or they can serve as a support layer for the staff you already have. AI assistants should be trained on the most basic tasks and issues related to your business so that they can handle low-priority problems.

For example, a tent rental company could program an AI assistant to answer the most basic questions that a potential customer might have. It would be trained on data and give information on different types of tents and guide customers to the right contact page for their requested tent type.

3. Task Automation

Businesses of any size, especially startups, can improve their customer service by automating routine tasks. One of the most commonly automated tasks is sending confirmation responses to customer emails, and another is sending follow-up responses to let customers know that their issue is in the process of being resolved.

Task automation will vary heavily depending on the exact business you run and the workflows of your business model. Start by breaking your everyday workflow into simple tasks that an AI tool can operate with little to no interaction from your staff. Automating routine tasks helps resolve customer issues faster and also leaves more time for your current staff to give personalized customer service.

4. Unified Support

To scale your business and improve your customer service at the same time, you should consider unifying your support systems. Startups and other small businesses tend to have customer communication broken up by mode of communication (e.g., phone calls, emails, contact form). However, using an omnichannel support structure unifies all of those into one ticketing system.

Unified support systems provide a higher level of customer service by segmenting customer issues. Emails, calls, and direct messages are converted into tickets and then separated by category or keyword. Customer service staff can then deal with high-priority issues first and resolve low-priority issues later.

5. Feedback Mechanisms

Lastly, your business should implement feedback mechanisms to make regular improvement part of your business model. Building a successful brand requires a loyal customer base, and those customers need to feel seen and heard. Regularly collect feedback from them through surveys, contact forms, and direct outreach.

Take action on any pressing and solvable customer issues, and continue to collect feedback so you stay up to date. You can also add tools that analyze collected customer feedback and identify problems before they become too big. For example, a tent rental business could have monthly strategy sessions to handle any persistent issues with recent rentals.

Key Takeaways

Improving customer experience often requires extra personnel, but there are several key ways that any brand can improve CX without adding headcount. Businesses can add knowledge bases to their websites, use AI assistants, automate routine tasks, establish unified support systems, and even implement feedback mechanisms. Startups and other small businesses should use these tools to boost their current system without worrying about hiring costs.

Global Business Expo

0

Startup Club is joining the Global Business EXPO! Connect with founders, builders, and business leaders from around the world, then stop by our booth to meet the community that’s helping entrepreneurs start, scale, and succeed.

Startup Time to Sell Index Rebounds as AI IPO Optimism Returns

The Startup Club Time to Sell Index (TTSI) has rebounded to 26.8 after falling to 16.8 in April amid concerns surrounding global uncertainty, geopolitical tensions, and the prospect of higher interest rates for longer.

The recovery has been surprisingly swift.

While many investors entered 2026 expecting continued volatility, sentiment has improved dramatically over the past several months. Much of that optimism has been fueled by growing anticipation surrounding the next generation of mega technology IPOs and the continued strength of the artificial intelligence sector.

Investors are closely watching companies such as OpenAI, Anthropic, and SpaceX, all of which have the potential to become some of the most significant public offerings of the decade. Whether these companies ultimately come to market this year or next, the prospect of their eventual public listings has helped restore confidence throughout the technology ecosystem.

Why does this matter to founders?

Because liquidity starts at the top.

When public markets are active and investors are confident, capital flows through the entire startup ecosystem. Public companies become more aggressive acquirers. Private equity firms gain additional liquidity and redeploy capital into new opportunities. Venture capital firms generate returns and raise larger funds to invest in the next generation of startups.

As liquidity increases, valuations often follow.

The Startup Club Time to Sell Index was created to measure these shifts in market sentiment and liquidity. Based on public listing activity, the TTSI provides founders with a simple way to gauge whether the market favors buyers or sellers.

At 26.8, the index remains firmly in buyer’s market territory. However, it is a significant improvement from the lows experienced in 2022 and a substantial recovery from April’s reading of 16.8.

The market is not yet signaling that founders should rush to sell. A true seller’s market would likely require a TTSI above 50. Nevertheless, the trend is encouraging.

From my own experience, timing can have an enormous impact on the value of a company. After spending a decade building a business to more than $180 million in value, I witnessed firsthand how quickly a market downturn can erase opportunity when the dot-com bubble burst.

That lesson ultimately inspired the creation of the TTSI.

Today, the data suggests we are no longer at the bottom of the cycle. The rebound in public listings, combined with renewed enthusiasm surrounding AI and large technology offerings, points to improving conditions for founders, investors, and acquirers alike.

The recovery is real.

The question now is whether the next wave of AI-driven public offerings can sustain the momentum and push the market closer to a true seller’s environment.

Best Books for Entrepreneurs: 14 Founder-Recommended Reads

When Colin C. Campbell asked his LinkedIn network to share the most impactful books in their entrepreneurial journeys, the responses revealed something deeper than just a reading list. They uncovered the principles, mindsets, and hard-earned lessons that shape how founders build, scale, and lead.

Here’s what stood out.

What Entrepreneurs Are Reading Right Now (And the Lessons That Actually Matter)

1. Crossing the Chasm – Geoffrey Moore
Synopsis: A guide to navigating the critical gap between early adopters and mainstream customers in technology markets.

Lesson I Learned: This book has had a profound impact on my career. It’s more relevant than ever given we are now in an AI world. Survival through the early adoption phase is critical. Understanding how to bridge that gap has been foundational in launching multiple successful companies as a serial tech entrepreneur.
Recommended by: Colin C. Campbell

2. The Goal – Eliyahu Goldratt
Synopsis: A business novel focused on identifying and solving bottlenecks within systems.

Lesson I Learned: Every business has one key bottleneck. Growth comes from fixing that constraint, not optimizing everything else.
Recommended by: Haider Malik

3. The Power Law – Sebastian Mallaby
Synopsis: Examines how venture capital shapes the startup ecosystem and outcomes.

Lesson I Learned: Venture capital dynamics shape outcomes as much as the founders themselves.
Recommended by: Michael Gilmour

4. Elon Musk – Walter Isaacson
Synopsis: A deep dive into the life and leadership of one of the most ambitious modern entrepreneurs.

Lesson I Learned: Vision combined with execution—and the ability to inspire talent—can drive extraordinary results.
Recommended by: Michael Gilmour

5. Man’s Search for Meaning – Viktor Frankl
Synopsis: A profound exploration of purpose, resilience, and human response to adversity.

Lesson I Learned: You cannot control everything, but you can control how you respond.
Recommended by: Dana Vanhoy

6. Quit – Annie Duke
Synopsis: Challenges the idea that persistence is always the answer, and explores the strategic value of quitting.

Lesson I Learned: Success is not just about grit. Knowing when to walk away is just as powerful.
Recommended by: Jonathan Jordan

7. The Millionaire Next Door – Thomas J. Stanley
Synopsis: Reveals how real wealth is built through discipline and long-term financial habits.

Lesson I Learned: True wealth is built quietly through discipline and tracking money, not flashy spending.
Recommended by: Martina Menard

8. The Wager – David Grann
Synopsis: A historical account of survival and leadership under extreme pressure.

Lesson I Learned: Leadership is more than a title—it is tested under pressure.
Recommended by: David Lovett

9. Upstarts / Amazon Unbound – Brad Stone
Synopsis: Chronicles the rise and scaling journeys of disruptive companies and leaders.

Lesson I Learned: Scaling companies face repeated patterns of challenge, growth, and reinvention.
Recommended by: Michael Gilmour and Colin C. Campbell

10. Finish – Jon Acuff
Synopsis: Focuses on setting realistic goals and overcoming perfectionism to actually complete what you start.

Lesson I Learned: Set goals that are enjoyable and achievable. Momentum comes from small wins, not perfection.
Recommended by: Jonathan Jordan

11. The Diary of a CEO – Steven Bartlett
Synopsis: A collection of insights on business, mindset, and personal growth through storytelling and interviews.

Lesson I Learned: Consistent learning and storytelling can build influence and long-term success.
Recommended by: Michael Gilmour

12. Big Little Breakthroughs  – Josh Linkner
Synopsis: Shows how small, consistent innovations lead to meaningful growth over time.

Lesson I Learned: Consistent small innovations compound into major growth over time.
Recommended by: Dave Rubinstein

13. The World is Flat – Thomas Friedman
Synopsis: Explores how globalization and technology have flattened the playing field for talent and opportunity worldwide.

Lesson I Learned: Access to global talent changes everything. This idea directly led to the creation of Geeksforless.com, built on tapping into skilled talent beyond geographic boundaries.
Recommended by: Colin C. Campbell

14. Be One of Zero – Karla Murphy
Synopsis: A perspective on achieving excellence through discipline, obsession, and high standards.

Lesson I Learned: Obsession can be a strength when directed properly. High standards are what turn ambition into results.
Recommended by: Karla Murphy

For entrepreneurs, the lesson is clear. Success is not built from a single idea or strategy. It is shaped by continuous learning, reflection, and the ability to apply the right insight at the right time.

If you’re building something today, the question isn’t just what you’re reading. It’s what you’re learning, and how quickly you’re applying it.

How to Catch the Next Tech Wave – Serial Entrepreneur

0

How to Catch the Next Tech Wave – Serial Entrepreneur

https://www.clubhouse.com/i/how-to-catch-the-next-tech-wave-serial-entrepreneur/C0tCcvds

EP218: The Simple Communication Shift That Makes Better Leaders

0

Why Great Entrepreneurs Speak Differently

In this episode of The Complete Entrepreneur, Colin C. Campbell and Michael Gilmour discuss how positive communication impacts leadership, startup culture, trust, and business growth. They share real stories from scaling companies, handling customer crises, leading teams under pressure, and building long-term relationships through intentional communication.

  • The power of positive language in leadership
  • Why founders should replace “I’ll try” with “I will”
  • How communication affects startup culture
  • Building trust through consistency and transparency
  • Why listening is an underrated entrepreneurial skill
  • Underpromising and overdelivering
  • Integrity, accountability, and leadership under pressure
  • How founders can communicate more effectively with teams and customers

The Simple Communication Shift That Makes Better Leaders

Why the way founders communicate shapes culture, trust, and growth

Most founders think strategy builds companies. In reality, communication does just as much.

The words you use every day with employees, customers, investors, and even yourself quietly shape the direction of your business. Over time, those words become habits. Those habits become culture. And culture eventually becomes momentum, either positive or negative.

That was the core theme in a recent conversation between entrepreneur and Start. Scale. Exit. Repeat. author Colin C. Campbell and entrepreneur Michael Gilmour. The discussion wasn’t about motivational slogans or surface-level positivity. It was about something much more practical.

“Communication is not separate from leadership. It is leadership.”

How founders speak directly affects how companies operate.

And once you start noticing it, you see it everywhere.

A founder says, “I’ll try.”

Another says, “I will.”

One creates uncertainty. The other creates confidence.

Small shift. Massive difference.

Great entrepreneurs speak differently

One of the most interesting parts of the conversation was how much language affects mindset itself. Colin explained that years ago, after hearing a speaker discuss “power talking,” he began intentionally changing the phrases he used in everyday business conversations.

Not because it sounded better.

Because it changed outcomes.

Instead of saying, “I have to get back to you,” he started saying, “I’d be happy to get back to you.”

Instead of saying, “I’ll try,” he began saying, “I will.”

Instead of using “but,” he replaced it with “and.”

The effect was immediate.

The tone changed. The energy changed. Even his own confidence changed.

Most founders underestimate how quickly negative language compounds inside a company. Teams absorb it. Customers feel it. Investors notice it. A founder who constantly speaks in uncertain or defensive language eventually creates uncertainty throughout the organization.

Positive communication isn’t about pretending problems don’t exist. It’s about approaching challenges with clarity, confidence, and ownership.

That’s leadership.

Trust is built in small moments

Entrepreneurs love talking about big wins. Funding announcements. Product launches. Growth milestones.

But trust is rarely built in those moments.

Trust is built quietly.

It’s built when you deliver something earlier than promised. It’s built when you communicate delays before customers have to ask. It’s built when people realize your word actually means something.

During the conversation, Colin shared a story about an ecommerce company whose reputation collapsed because leadership consistently overpromised delivery timelines. Customers were told products would arrive quickly. Instead, delays stretched into months.

The issue wasn’t just operational.

It was emotional.

Customers stopped believing the company.

That’s why the old principle of “underpromise and overdeliver” still matters so much in startups. It sounds simple because it is simple. But very few companies consistently do it.

Founders often overpromise because they want to impress people. In reality, reliable communication is far more impressive than exaggerated promises.

Great operators understand this instinctively.

They protect trust at all costs.

Listening is one of the most underrated startup skills

Most people spend conversations waiting to speak.

Very few actually listen.

Michael Gilmour talked about using a communication technique called mirroring, where you repeat the last few words someone says back to them as a question. It sounds simple, but it changes conversations immediately because people feel heard.

And that matters more than founders realize.

Customers want to feel understood before they want solutions. Employees want to feel respected before they want direction. Partners want to feel heard before they commit.

The best entrepreneurs aren’t always the loudest people in the room.

They’re often the best listeners.

One story from the discussion stood out. Michael explained how he intentionally used listening techniques with his daughters during dinner one evening instead of dominating the conversation or offering advice. Afterwards, they commented on how connected they suddenly felt to him.

Nothing dramatic changed.

He simply listened.

That’s a powerful reminder for founders who spend most of their lives pitching, presenting, and persuading. Sometimes the strongest move in business is slowing down long enough to truly hear people.

Optimism without honesty destroys credibility

There’s a fake version of positivity that shows up constantly in startup culture.

Blind optimism.

The “everything is amazing” founder who ignores reality eventually loses trust from employees, customers, and investors alike. The best leaders don’t avoid hard truths. They face them directly while remaining confident they can solve the problem.

That distinction matters.

Colin shared a story about walking into a tense meeting with Vodafone after major technical issues impacted customers. Instead of defending the company or avoiding responsibility, he immediately apologized and presented a plan to fix the issue.

The dynamic in the room changed instantly.

Because honesty changes conversations.

Customers can handle problems. Teams can handle setbacks. Investors can handle delays.

What people struggle with is silence, excuses, and spin.

Transparency builds confidence even during difficult moments.

In many cases, especially in startups, the way you handle mistakes matters more than the mistake itself.

Integrity compounds faster than revenue

One line from the conversation captured the entire philosophy perfectly:

Integrity over money.

Not sometimes.

Always.

Colin talked about firing a salesperson who lied to a customer even though the lie initially appeared to save the company money. Short-term wins built on dishonesty eventually become long-term liabilities.

Founders who compromise integrity early almost always pay for it later.

The culture weakens.

Trust disappears.

Good employees leave.

Customers stop believing what they hear.

Strong companies are built on consistent behavior, not clever messaging.

That’s why communication matters so much. The words leaders choose reveal what the company actually values.

And teams notice everything.

The founders who last communicate with intention

The entrepreneurs who build enduring businesses usually have one thing in common. They communicate intentionally.

They understand that leadership is not just strategy meetings and decision-making frameworks. Leadership is how you show up during difficult conversations. It’s how you respond under pressure. It’s how you speak to customers when something breaks. It’s how you treat employees when mistakes happen.

Words shape culture long before policies ever do.

That’s why positive communication is not soft leadership. It’s operational discipline.

The best founders understand something many people miss:

Every sentence either builds trust or weakens it.

And over time, those moments define the company.