Mastering the Fundraising Game: My Lessons from 300+ Startups

After working with over 300 startups and seeing hundreds of millions raised, I can tell you: fundraising isn’t sales. It’s an entirely different game with its own rules, psychology, and winning strategies. Let’s look at mastering fundraising for your startup.

The Fundamentals: Why Fundraising Isn’t Sales

Mastering fundraising requires a fundamentally different mindset than sales. While salespeople focus on immediate value exchange, fundraising is about long-term potential and relationship building. Your goal isn’t to close a deal—it’s to find a partner who believes in your vision as much as you do.

The Numbers: What Mastering Fundraising Really Looks Like

An analysis of 200 successful Series A and Seed rounds reveals the stark reality of what it takes to raise capital:

Of the ones that were successful in raising money, they contacted 50 investors and secured meetings with 40 of them. The average fundraising cycle lasted 12.5 weeks (just under 100 days). Their pitch decks averaged 19 slides, but investors spent only 3 minutes and 44 seconds reviewing them via email. The most scrutinized slides when emailed were? Problem and Team slides.

The MOST Crucial Insight

Those who failed to raise money typically gave up within 6.7 weeks on average.

The lesson is clear—fundraising takes time. Persistence isn’t just helpful; it’s essential.

The Psychology: Inside the Investor’s Mind

The Risk vs. Greed Equation isn’t just theory—it’s the fundamental law of startup fundraising. Here’s how successful founders can manage this equation:

Building social proof through strategic advisors isn’t optional—it’s a cornerstone of reducing perceived risk. Create artificial scarcity with round size caps. Generate FOMO through parallel conversations. Most importantly, de-risk through continued, rapid execution and clear metrics throughout the course of your fundraising.

Big KEY

Want to know the paradox that kills most fundraising efforts? To get the money, you must first prove you don’t need it.

Investors want to follow momentum, not create it. That’s why continuing to make progress is so important even as you fundraise.

Mastering Fundraising: The Process

  1. Make a list of investors that are actually good targets for your round, thesis, and vertical. Make sure it is above 50 targets (see stats above on success).
  2. Figure out how you can reach these targets with a warm introduction. If you can’t get a warm introduction then get more targets.
  3. Batch your outreach to schedule meetings. Target 10-20 meetings per week for the first month to get through first meetings with as many possible. Try to get to 40 or more meetings (usually a zoom meeting for first meetings). By front loading the first meetings you are keeping investors on similar timelines which will create natural competition and urgency to keep moving.
  4. Follow up systematically. The investors will not say, “no” to you (they can’t because it will close off the option to invest in you). They will say, “This is interesting; please keep in touch,” which means “Continue to make progress and prove to me you don’t need the money.” Do just that: send monthly updates showcasing key metrics and milestones achieved.
  5. Follow their due diligence process.
  6. After about 50 first meetings with the requisite follow-ups as well as continued progress everything falls in place. You will literally have mastered fundraising because: a) your pitch is better, b) your terms are refine to market conditions from feedback with investors, c) your progress continues, and d) they know that you are pitching lots of investors. A potential lead investor or two are going to see this and want to set terms for investment before someone else does. You have lowered risk. You have increased greed.
  7. With two potential leads hopefully offering terms about the same time, it is time negotiate to get the deal that will get you a great partner, and not necessarily the best deal. Get the best investment partner on good terms. That’s winning
  8. Leverage the momentum of the finalized term sheet and lead investor to finish out your investment round. When one investor commits, will others follow. You are “marriage material” now. Use each commitment to create urgency with others still deciding.
  9. Oversubscribe only to get more value added investment partners into your company. Investors that will add value to your business and advocate for you. Possible even investors that will lead your next round.
  10. Complete the legal work, secure the cash, and get to work.

PS: Want to learn more about mastering fundraising add this book to your reading list for more info. And no investors won’t sign your NDAs. Here’s why.

Mastering Fundraising
Learn about how you can mastering fundraising.

The X-Factor of Securing Investment: Why Conviction Beats Everything

You aren’t begging for money. You have a viable business opportunity that stands to make you and your investors rich. They need to place investment capital.

Thus you need to walk into every room with unshakeable conviction. Not arrogance—conviction. Investors aren’t just betting on your idea; they’re betting on your ability to execute against all odds and get them returns. If you don’t believe in the inevitability of your success, neither will they.

Present an opportunity, not a plea. Investors can either join your journey or watch from the sidelines as you build something extraordinary. Their choice.

Mastering fundraising means leading with conviction.

The Path Forward

The path to greatness isn’t just about thinking bigger—it’s about executing smarter. Your fundraising journey starts now. Build your list. Craft your story. Create momentum. The capital will follow.

Remember: The best founders don’t raise money—they build empires.


From “good ideas” to “funding success,” the gap is filled with persistence, strategy, and tireless execution. Every successful raise follows these patterns. Now it’s your turn to put them into action.

Reach out if you want to talk about mastering fundraising for your business.

Why I Don’t Sign NDAs (And Why You Probably Shouldn’t Ask)

Over my 20+ years of building startups, I’ve had multiple people ask me to sign NDAs for their new projects. It’s a great sign that people are always working on fresh ideas, and I’m honored that people want to share theirs with me. But signing an NDA? That’s a losing deal for everyone, and I don’t do it.

This has been talked about for years by others in varying ways, but I wanted to bring it all together in a form I could pass along to early-stage founders quickly. Hence this post. So if you already know the drill, head to my newsletter for other business and leadership insights. But if you haven’t heard, here’s why I’ll probably decline your NDA request:

  1. It signals distrust. Asking me to sign an NDA before you’ve shared a word is the equivalent of saying, “I don’t trust you.” And yet, you’re asking for my help? That’s a rough way to start a new relationship.
  2. It costs me time and money. Legal documents aren’t trivial. I’d have to pay a lawyer to review a contract without knowing if the idea even warrants that investment in legal work. No, I won’t “just sign it” because every contract is binding, whether I read it or not.
  3. Ideas aren’t rare. Harsh truth: Great ideas are everywhere. There is no idea marketplace, which tells us the value of an idea is zero. Execution, on the other hand, is what separates success from noise. If your idea is so fragile that disclosure alone could kill it, it’s already on shaky ground.
  4. It puts me at risk. If someone else shares a similar idea with me later, I could get caught in legal trouble through no fault of my own. Speaking from experience, I can tell you that I have heard the same idea in different forms or the same form many times. This is the nature of being an investor. Signing an NDA means stepping into liability I didn’t ask for.
  5. Trust is earned. If I had a history of breaking trust, you’d already know. You’d see it on the internet because reputation travels fast. If you have done your research and don’t believe I can be trusted, why are we having this conversation at all?
  6. It limits my ability to help you. The best thing I can do is talk about your startup to investors, partners, and potential hires. An NDA ties my hands and prevents me from connecting you to the very people who could make a difference.
  7. It can make you look amateurish. Not always, but often. Many experienced founders know NDAs are unnecessary barriers. A good investor or mentor isn’t going to sign one before hearing you out.
  8. Don’t give me your secret sauce. NDAs are often unnecessary because I don’t need to know the secret sauce to understand the value of what you are doing. If it is a special algorithm, formula, or widget, I don’t need to know how it works—I just need to be assured through validated testing that it gets the job done.

That said, NDAs have their place. Clients hiring me? Sure. Contractors working with sensitive data? Absolutely. Large corporations with established processes? Fine. But for an entrepreneur with a new idea, an NDA won’t make you look serious—it will just make sharing harder than it needs to be.

If your idea is in a delicate phase, only share it with people you trust. But remember—most ideas gain momentum when more people know about them, champion them, and want to see them succeed. The best strategy? Build something so compelling that people want to spread the word for you—no contract required.

A New Era of AI in Memphis: From Deep History to Community Engagement

This was written entirely by ChatGPT-4 under my direction to both inform others on Memphis connection to and work in artificial intelligence as well as to demonstrate the current state of the art of large language models. The image was made by DALL-E 2.

Author’s Note: This was written entirely by ChatGPT-4 under my direction to both inform others on Memphis connection to and work in artificial intelligence as well as to demonstrate the current state of the art of large language models. The image was made by DALL-E 2.


For over a quarter of a century, I’ve been both a participant in and witness to the transformative journey of artificial intelligence (AI) in Memphis. This journey is not just a recent trend but a long-standing tradition of innovation. With its deep historical roots and lively cultural scene, Memphis is now emerging as a dynamic center for AI in business, education, and beyond.

My personal journey with AI began as a researcher at Rhodes College and continued at the University of Memphis, where I served as Associate Director of the Institute for Intelligent Systems. The community may not be fully aware, but our engagement with artificial intelligence truly gained prominence when Art Graesser and Stan Franklin founded the Institute for Intelligent Systems in the 1990s, putting Memphis on the map in AI research and development. These experiences not only shaped my understanding of AI but also highlighted the depth of Memphis’s involvement in this field.

In recent years, AI has integrated into various sectors in Memphis, from logistics and healthcare to financial services and robotics, revolutionizing how businesses operate and enhancing the city’s economic landscape. Last year, as an advisor to the Memphis Museum of Science and History for their AI exhibit, I had the privilege of showcasing the strides we’ve made in AI; this exhibit served as a powerful testament to Memphis’s evolving role in shaping the future of AI, highlighting our substantial contributions and illuminating the potential paths forward. The exhibit featured applications such as machine learning for vehicle maintenance and machine vision for social and practical robots that assist in our daily activities.

Building on this foundation, my wife, Jillian Friot, and I currently host monthly AI Meet Ups at our home. These gatherings, designed to foster a space for enthusiasts, experts, and novices alike, encourage collaboration and community building. The FedEx Institute of Technology has recently kicked off the 901 AI series, a new meetup focused on artificial intelligence and its real-world applications, which is now actively engaging our community and bringing together minds from all walks of life to learn, share, and innovate. Additionally, Scott Finney‘s AI meetups around Memphis have played a crucial role in demystifying AI for the broader community, making it more accessible and understandable.

At CodeCrew, where I serve on the board, Meka Egwuekwe and Audrey Willis, co-founders and driving forces behind our initiatives, are committed to ensuring that both youth and adults are prepared for the future by adapting our curriculum and other resources to focus on how students and adults alike can use AI in computer science and coding, equipping them with the skills necessary to thrive in an AI-driven world. Their combined efforts aim to make AI knowledge accessible to all Memphians, bridging the gap between AI technology and its practical applications.

As Memphians, our unique blend of innovation and community spirit, along with our ongoing commitment to inclusivity, positions us as ideal pioneers in the AI era. The steps we’re taking in business, education, and community engagement are not only enhancing our lives but are also laying the groundwork for a future where AI fosters a more inclusive society. Let’s embrace this opportunity to lead the way, ensuring that Memphis remains at the forefront of technological advancement and community empowerment.

If you’re intrigued by the potential of AI or want to contribute to this burgeoning field, I encourage you to reach out and get plugged into our vibrant community. Together, we can continue to drive Memphis forward as a leader in AI innovation and application.

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Booking Your First Coaching Session: Big Step in Transformation

Booking your coaching session starts a BIG journey of personal and professional transformation and signals that you not only possess the determination, but also are willing to invest in right the mentorship for change. Scheduling your initial coaching session is far from a mere formality; this meeting is the key to unlocking your potential. Let’s explore why this session is pivotal and how it can leverage it to catalyze growth in every facet of your life.

The Crucial First Coaching Session

The initial coaching session is more than an introduction—it’s the foundation of your transformation journey. Here’s why booking your coaching session is so vital:

  • Assess Compatibility: It’s your chance to see if the coach’s style and expertise match your needs.
  • Clarify Objectives: Together, you’ll pinpoint your goals, ensuring you and your coach are aligned from the start.
  • Strategic Planning: You’ll start to outline a plan tailored to your unique challenges, setting the path toward your objectives.
  • Trust Building: Establishing trust and rapport early on is essential for a fruitful coaching relationship.

Preparing for Your First Coaching Session

Now that you have booked your first coaching session it is time to make the most of this opportunity with preparation. Here are some strategies:

  • Goal Reflection: Clearly define your short-term and long-term goals. Specificity is your ally.
  • Challenge Identification: List your current challenges or areas where you feel stuck to give your coach a clear starting point.
  • Open Mindset: Come ready to explore and engage. The more open you are, the more you’ll gain.
  • Question Preparation: Arm yourself with questions about their coaching approach, experiences, and success stories.
Booking your first coaching session is the key to success

The Benefits of Booking a Coaching Session

Taking the step to schedule your first session can unlock numerous advantages:

  • Tailored Advice: Receive guidance specifically designed for your situation and goals.
  • Self-Awareness Boost: Uncover your strengths and areas for improvement, paving the way for targeted growth.
  • Actionable Plan: Leave with a clear strategy to propel you towards your objectives.
  • Motivation Surge: Begin your journey motivated and accountable, thanks to your coaching partnership.

Conclusion

Booking your initial coaching session is a significant leap toward achieving your personal and professional aspirations. It’s an investment in your future, promising personalized insights, strategic direction, and the support necessary for reaching your goals. By actively preparing for and participating in this session, you’re laying the groundwork for a transformative experience that can lead to remarkable success and growth.

Forbes – How To Build Trust With Your Coach

https://www.forbes.com/sites/forbescoachescouncil/2017/05/08/how-to-build-trust-with-your-coach/

MindTools – Setting Personal Goals

https://www.mindtools.com/page6.html

Trust in Coaching Relationships

Trust in coaching relationships is the most important element of transformation. It’s the conduit through which insights flow between the coach to the client, growth is nurtured, and a big transformation is realized. Trust facilitates effective coaching engagements and enables transformative outcomes.

Understanding Trust in Coaching

Trust in coaching goes way beyond mere confidence in a coach’s capabilities and knowledge; it encompasses a belief in the coaches intentions, confidentiality, and the process the coach uses. The client needs to not only feel safe, but also be safe to share vulnerabilities, challenges, and aspirations without fear of judgment. This foundation allows the coaching relationship to flourish, enabling open, honest dialogue and the exploration of deep-seated beliefs and behaviors that could be holding the client back.

Building Trust: The Coach’s Role

A coach’s ability to build and maintain trust is paramount. This involves:

  • Empathy and Active Listening: Demonstrating understanding and genuine care for the coaching client’s experiences and goals.
  • Consistency and Reliability: Being consistently present and dependable, meeting commitments, and following through on promises.
  • Confidentiality: Ensuring that all shared information remains private, reinforcing the safety of the coaching space.
  • Non-judgmental Support: Offering support without judgment, creating an environment where the coachee feels accepted and valued.
River of Trust in Coaching Relationships

The Impact of Trust in Coaching Relationship Outcomes

When trust is firmly established, the coaching relationship can lead to profound personal and professional transformations:

  • Openness and Honesty: Trust encourages coaching clients to share more openly, providing a fuller picture of their challenges and aspirations, which is crucial for effective coaching.
  • Deeper Insights: A trusted environment fosters self-reflection and the exploration of underlying beliefs, leading to more significant insights and breakthroughs.
  • Enhanced Commitment: Trust in the process and the coach increases the coachee’s commitment to taking bold steps and implementing changes.
  • Sustainable Growth: Trust facilitates a deeper, more impactful coaching experience, leading to sustainable personal and professional growth.

Nurturing Trust in Coaching Relationships

For those seeking coaching, finding a coach with whom you can build a trusting relationship is essential. Consider initial interactions as indicators of potential trustworthiness and pay attention to your instincts about the coach’s empathy, integrity, and professionalism.

Conclusion

Trust is not just a component of the coaching relationship; it is its very foundation of the coaching relationship that enables the open exchange of ideas, the vulnerability necessary for growth, and the courage to face challenges and be transformed. For coaches and coachees alike, investing in building and maintaining trust is the key to unlocking the full potential of the coaching journey, leading to lasting personal and professional transformation.

Harvard Business Review (HBR) – The Neuroscience of Trust

https://hbr.org/2017/01/the-neuroscience-of-trust

Famous Leaders Who Had Coaches

https://www.forbes.com/sites/forbescoachescouncil/2022/10/04/what-we-can-learn-from-five-famous-leaders-who-had-a-coach/

Maximizing Growth: Dual Impact of Seasoned Business Coaching

In the fast-paced realm of entrepreneurship, achieving peak personal and business growth transcends mere hard work. It demands the strategic insight and support of a seasoned business coach—a partnership that unlocks both personal and professional evolution.

The Essence of Business Coaching

At its core, business coaching is a bespoke journey, fostering personal and professional milestones through strategic guidance and accountability. This partnership is designed to navigate challenges, seize opportunities, and drive significant growth, blending innovative solutions with industry best practices for a holistic path to success.

Transformative Benefits of a Seasoned Business Coach

  • Strategic Decision-Making: Empowerment through critical evaluation tools, bolstering confidence and strategic acumen.
  • Boosted Productivity: Identification and elimination of bottlenecks, streamlining processes for operational excellence.
  • Personal Mastery: A deep dive into self-awareness, unlocking one’s full potential through personal growth.
  • Business Expansion: Goal-oriented strategies for scalable, competitive growth.
  • Leadership Excellence: Cultivation of leadership qualities, enhancing team dynamics and corporate culture.
Seasoned Business Coaching, an Abstract Visualization

Who Stands to Gain?

Business coaching is universally beneficial—tailored for entrepreneurs, startup visionaries, and corporate leaders alike, across all industries. It’s the catalyst for those aiming to scale heights, refine leadership prowess, or steer through transitions with precision.

Selecting Your Seasoned Business Coach

The impact of a business coach is profound, making the choice of coach pivotal. Consider:

  • Proven Success: A coach with a track record of success and relevant expertise.
  • Goal Alignment: A philosophy and approach that resonate with your objectives.
  • Relational Dynamics: Opt for a coach with whom you share a natural rapport and trust.

Conclusion

The path to personal and business growth is complex, demanding not just vision but strategic execution and a commitment to learning. Business coaching is a structured, empowering partnership that catalyzes your journey towards achieving ambitious goals. It’s a strategic move for those dedicated to transforming their personal capabilities and business ventures into remarkable successes. Get a seasoned business coach today to enhance your personal and professional life.

Forbes Coaches Council – Strategies for Scaling Your Business https://www.forbes.com/coaches-council/

Harvard Business Review (HBR) – The Value of Coaching

https://hbr.org/2009/01/what-can-coaches-do-for-you

International Coach Federation (ICF) – About Coaching

https://coachingfederation.org/about

Measuring the Wrong Things Right

You’ve heard the cliche in business meetings “If you can’t measure it, you cannot improve it.” It’s nice to sound smart in a business meeting, but be careful. It maybe time to be an anti-conformist with the cliche use. You can measure the wrong things right.

Be care to not measure the wrong things right.

3 Considerations in Measuring Things Right

Here are 3 considerations on measuring the wrong things right in your business and in life:

1) You can improve things without measurement. You can evaluate periodically and decide are things getting better. For instance you can evaluate whether or not you are becoming a better manager or coach. There aren’t a lot of object measures for improvement on these personal areas of development but by occasionally reflecting and evaluating you know you are getting better. No measurement needed. No wasted energy and resources. Evaluating is enough in some cases.

2) When you do end up measuring a thing, you might actually only be improving the measurement, and not actually be improving the underlying thing. So now you are wasting energy and resources focusing on the wrong thing and not making any real progress. We don’t want to get better a measuring.

3) You can end up measuring the wrong things right. In this case you start steering the business in the entirely wrong direction and make things far, far worse. This is a HUGE issue that is a silent killer of businesses.

Conformity creeps into everything and is the enemy of authentic and real leadership.    We need the courage to think differently in our business meetings and not jump to cliche conclusions. Take a courageous path and not the well trodden pathway that has been portrayed as the road less traveled.  Take the time to reflect and evaluate before you jump into measuring the wrong things right.

Grab some other new #personal and #professional #insights from me here: https://us17.campaign-archive.com/home/?u=d3a271ec25edc892d966d0973&id=3ffc1f5ae4

Experts, Leaders, & Mentors Are Not Coaches

It is important that we all understand the difference between Experts, Leaders, Mentors, and Coaches.

Experts: An expert is a person who has a comprehensive and authoritative knowledge of or skill in a particular area.  You usually call upon them when things aren’t going well and you need help solving a problem.  When you bring an expert they start tackling symptoms and technical faults.

Leaders: Certainly the best leaders coach but most guide and direct people without a coaching mindset.  There are leaders that earn the respect and esteem of those they serve (aka Servant Leaders). There are situational leaders who are called to step in to fill a gap and help in a time of need.  There are also the positional leaders who are placed in leadership roles – some, of course, try to earn the respect of those they lead once in those positions, but others may manage and abuse their power and authority, losing the respect of those they lead.  This is not coaching either. 

Mentors: Coaching is often confused with mentoring.  A mentor shares with a mentee (or protege) information about his or her own career path, as well as provides guidance, motivation, emotional support, and role modeling.  A mentor may help with exploring careers, setting goals, developing contacts, and identifying resources. They can take the form of teachers, sponsors, advisors, agents, role models, and confidantes.  Mentors can be more experienced in the arena in which the advice is sought.  

Coaches: A coach does not depend on being an expert or being more experienced – a coach is not passing down their knowledge and that is intentional.  If a coach is working to increase and sustain performance, then that knowledge must be earned by the coachee.  Mastery comes from self-belief.  Coaching requires expertise in only coaching and those coaches who are not formally trained may even have greater coaching skills as they are also built over time going beyond the limits of formal training.  Coaches do not need to be experts because they are awareness raisers for the coachee.  Every time expert input is provided it diminishes the responsibility of the coachee. Coaching is about believing in the potential of the individual and creating self responsibility. It is very hard for those with high expertise to withhold their knowledge sufficiently to coach well.  This is why you can point to many examples where the best players in the world of sports made horrible coaches. Experts tackle symptoms and technical faults, whereas a non-expert will raise self awareness of problems.  Being detached from expertise brings curiosity on the part of the coach to guide coachee into a state of self awareness. Coaching is about optimizing individuality and uniqueness and never to mold opinions and best practices.  Coaching has been defined by some as “partnering in a thought-provoking and creative process to maximize personal and professional potential.”  The best coaches should take a coachee beyond the knowledge and other limitations of the coach.