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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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.
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.
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
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:
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Are you a founder, entrepreneur, or CEO who built a business to create freedom, only to find you've created a high-stress job for yourself?
If you're being honest, you're the bottleneck. You spend your best hours trapped in your inbox, playing calendar Tetris, and doing low-level tasks you know you shouldn't be doing. You have brilliant ideas for growth, but they die on the vine because you're too busy putting out fires and managing the day-to-day.
It's a frustrating cycle: you can't grow without more help, but you don't have the time to find, hire, and train that help. The painful truth is that your business can no longer grow beyond your personal capacity.
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One minute you’re unstoppable. The next, you’re questioning everything. Building a business is exciting, exhausting, & personal. Sharing stories of the highs and lows, and staying resilient.
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