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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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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

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

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

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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.

EP220: When Business Gets Hit by Forces Outside Your Control

Entrepreneurs are often hit hardest by forces they never saw coming: rising interest rates, tariffs, government policy changes, supplier disruptions, market collapses, and even personal crises outside the business. In this episode, the conversation centers on a simple but difficult truth: founders cannot control the external environment, but they are responsible for how they respond.

AI Growth Hacks Every Entrepreneur Should Be Using Now

AI is no longer a future-facing technology reserved for large companies, technical teams, or venture-backed startups. It has become a practical operating tool for entrepreneurs who need to move faster, cut costs, test ideas, and make better decisions with fewer resources.

But the real advantage does not come from simply “using AI.” The advantage comes from knowing where to apply it, how to question it, and when to slow down enough to verify the output.

For entrepreneurs, AI is becoming less of a novelty and more of a business partner. It can draft documents, analyze data, create workflows, organize information, generate ideas, and help founders move through roadblocks that once required expensive outside help. The key is to treat it as leverage, not magic.

Use AI to Reduce Professional Service Costs

One of the clearest uses of AI is preparing the first version of complex business documents.

Entrepreneurs often pay thousands of dollars for legal, financial, or strategic documents before they even know whether an idea has traction. AI can now help draft early versions of private placement memorandums, business plans, investor summaries, operating procedures, internal policies, and vendor briefs.

That does not mean lawyers, accountants, or consultants disappear from the process. It means their role changes. Instead of paying someone to create everything from scratch, founders can bring a strong first draft and ask the professional to review, correct, structure, and finalize it.

This shifts the cost structure. Service providers who use AI well will become more valuable because they can deliver better work faster. Service providers who ignore it may become harder for small businesses to justify.

Turn Messy Operations Into Structured Data

AI is especially useful when a business has information scattered across photos, emails, PDFs, spreadsheets, receipts, or notes.

A furnished rental operator, for example, can photograph furniture and appliances, ask AI to identify the items, estimate replacement values based on a target retailer or quality level, and organize everything into a spreadsheet. What used to require manual inventory work can become a repeatable workflow.

The same principle applies to receipts, asset lists, maintenance logs, customer support records, marketing reports, and internal documentation. AI can help convert unstructured information into usable business data.

The important step is review. AI can estimate, categorize, and organize, but the entrepreneur still needs to verify the output before using it for insurance, accounting, purchasing, or financial planning.

Go Beyond Surface-Level Marketing Metrics

Many founders track metrics like return on ad spend, clicks, impressions, and conversion rates. Those numbers matter, but they can be misleading if viewed in isolation.

AI can help build deeper marketing analysis systems that connect ad performance to contribution margin, customer lifetime value, repeat purchase behavior, pricing, fulfillment costs, and cash flow timing.

A campaign may look profitable based on revenue alone, but if the margin is weak or the second purchase happens two years later, the business may still be losing money in the short term. AI can help founders create more thoughtful dashboards and decision frameworks around when to scale, pause, or cut spend.

This is where AI becomes more than a reporting tool. It becomes a thinking partner that helps ask better business questions.

Build Agents, But Keep Humans in Control

AI agents are becoming a major area of experimentation. They can help automate email follow-ups, bookkeeping workflows, customer support, research, reporting, and project management.

Tools like n8n, LangGraph, Pinecone, pgvector, Claude Projects, ChatGPT Projects, NotebookLM, and other agent frameworks are making it easier to connect AI with business data and recurring tasks.

But automation introduces risk. Agents can misread documents, misunderstand instructions, create incorrect classifications, or build on earlier mistakes. In finance, legal, customer-facing support, and analytics, those errors can compound quickly.

The best approach is not full blind automation. It is supervised automation. Let AI perform the repetitive work, but build in human review, confidence thresholds, source checks, audit trails, and escalation rules.

AI should not be treated as the boss. The founder, operator, or subject-matter expert still owns the decision.

Use AI for Ideation and Early Validation

AI can also help founders explore business models they might not have considered.

A co-living operator looking to reduce furnishing costs may discover local “Buy Nothing” groups, secondhand sourcing strategies, or leasing arbitrage models through AI-assisted brainstorming. A founder building a new product can use AI to simulate landing pages, mockups, scripts, decks, and customer journeys before investing heavily in development.

This is one of AI’s strongest uses: helping entrepreneurs test before they build.

But there is a trap. AI makes it easy to create endless plans, decks, mockups, workflows, and content. That can feel productive while avoiding the harder work of getting customers, generating revenue, and validating demand.

The goal is not to become busy. The goal is to move the business forward.

Create a Better Knowledge System

Tools like NotebookLM show how powerful AI becomes when it is grounded in specific source material. Instead of asking a general AI model for broad answers, founders can upload documentation, books, transcripts, policies, help files, or internal notes and query that trusted information directly.

This is useful for training, research, customer support, onboarding, content creation, and internal operations. It also reduces the risk of irrelevant or unsupported answers because the AI is working from a defined knowledge base.

For best results, source quality matters. Clean documents, markdown files, text files, structured notes, and well-organized references usually produce better outputs than messy PDFs or incomplete uploads.

The Real Growth Hack Is Better Judgment

The entrepreneurs who benefit most from AI will not be the ones who ask it to do everything. They will be the ones who learn how to direct it.

That means writing better prompts, giving clearer context, checking sources, questioning assumptions, and knowing enough about the task to spot weak answers. It also means building systems where AI supports human intelligence instead of replacing it.

AI can save time. It can lower costs. It can unlock ideas. It can make small teams look much larger. But it still needs direction, judgment, and accountability.

The best founders will use AI as a multiplier for what they already know—and as a guide for learning what they do not.