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.

What Is the Isolation Tax in Leadership?

What Is the Isolation Tax? Isolation isn’t just a social issue—it’s a career and business killer. Think of the biggest breaks and insights that impacted your life. How many came out of the blue or by chance? A shot in the dark? Probably not many. They came from meaningful connections, deep conversations, and people that challenged your thinking.

Isolation of a Business Leader
Isolation of a Business Leader

The problem is we are getting more and more isolated as a society. What’s worse for business leaders is there are fewer and fewer people with whom you can have real, trusting conversations who aren’t also vested in the outcomes. As a result, you become more isolated the higher you go and the more successful you get.

Yet you can’t leave your personal and professional growth to chance and face the isolation tax alone.

What Is the Isolation Tax and How Does It Manifest as a Cost?

  • Missed Opportunities – Without a strong network and trusted thought partners, business leaders miss out on deals, collaborations, and career-defining moments.
  • Slower Decision-Making – Lacking diverse, objective perspectives can lead to hesitation, second-guessing, and costly mistakes.
  • Stagnation – Without outside challenges, leaders risk reinforcing their own blind spots, making it harder to grow and innovate.
  • Emotional and Mental Strain – Leadership can be lonely, and without trusted advisors, the stress can lead to burnout and poor decision-making.
  • Aid for the Extrovert – Many leaders are extroverted thinkers and literally need to think outloud, but the walls don’t talk back. You need someone you can trust to help you speed up your think by being present.

The “Isolation Tax” in Action

  • The Business Owner – Running a company can be an echo chamber. Without external advisors, you may struggle to see inefficiencies or new market opportunities.
  • The CEO/Executive – The higher you climb, the fewer people will tell you the truth. A thought partner ensures you hear what you need to hear, not just what others think you want to hear.
  • The Entrepreneur – Investors and employees have vested interests. A coach or mentor helps you navigate critical decisions without bias.
  • The Professional in Transition – Making a career pivot without external insights can lead to missteps. A mentor, coach, or thought partner accelerates the process and reduces risk.

How You Can Reverse the Isolation Tax

  • Engage a Thought Partner or Advisor – A trusted external perspective brings fresh insights, constructive challenges, and strategic thinking.
  • Build a Personal Advisory Board – Surround yourself with experienced mentors, peers, and experts who provide objective guidance.
  • Invest in Personal and Professional Coaching – A coach helps you break out of isolation, sharpen your vision, and accelerate your success.

The Smartest Investment You Can Make

For those experiencing the isolation tax—especially in matters that intersect both personal and professional growth—coaching isn’t an expense; it’s a capital investment in yourself. The most expensive thing you’ll ever pay for is isolation. The best way to avoid it is by getting a coach.

Get connected to get ahead.

Ready to break free from the isolation tax? Let’s start the conversation.

Grab a free coaching session with me here.

Guide to Unlock Your Potential

Embark on the journey of personal and professional development with this guide to unlock your potential. Whether you’re an entrepreneur, a business leader, or a professional aiming to elevate your career, understanding how to fully tap into your capabilities is essential — it is time to unlock your vast and full potential within. This guide provides actionable strategies and insights for achieving transformative growth and success in both your personal life and business endeavors.

Exploring Personal and Business Potential

Maximizing potential means harnessing your innate talents and applying them towards your aspirations. It’s a process of breaking barriers, overcoming challenges, and realizing your true capacity for growth. In the business world, this translates to career advancement, fostering a culture of innovation, and driving continuous improvement.

Strategy Guide to Unlock Your Potential

  • Self-Assessment and Goal Setting: Start with a deep dive into your strengths and weaknesses. Establish clear, attainable goals that reflect your vision for success.
  • Lifelong Learning: Embrace continuous education. Stay updated with industry trends and expand your skill set through courses, workshops, or self-directed learning.
  • Mentorship and Coaching: Leverage the insights and support from mentors or coaches. These relationships can provide personalized advice, foster strategic thinking, and help overcome obstacles.
  • Networking: Cultivate a robust professional network. Engage in partnerships and collaborations that offer fresh perspectives and opportunities for growth.
  • Wellness and Balance: Prioritize your health and well-being to sustain success over time. Achieving a healthy work-life balance boosts productivity and satisfaction.
  • Adaptability and Resilience: Develop the ability to adapt to change and recover from setbacks. These skills are crucial for capitalizing on opportunities and maintaining progress.
  • Strategic Planning: Craft a detailed plan for your personal and business goals. Focus on efficient resource management, task prioritization, and flexible strategies to stay aligned with your objectives.

The benefits of using the guide to unlock your potential are below.

A guide to unlocking your potential.

Benefits from the Guide to Unlock Your Potential

Committing to your personal and business potential can yield remarkable benefits:

  • Elevated Performance: Enhance your productivity by playing to your strengths and addressing weaknesses.
  • Staying Competitive: Keep ahead in a fast-paced market through innovation and continuous learning.
  • Personal Satisfaction: Find fulfillment in achieving your goals and realizing your potential.
  • Business Advancement: Drive growth and success with strategic planning and resilience.

Conclusion

This guide to unlock your potential is just the start. The journey is ongoing and dynamic, demanding dedication and strategic action. By adopting the strategies highlighted in this guide, you embark on a transformative journey towards unparalleled success and fulfillment in all aspects of your life.

Harvard Business Review – The Value of Mentoring

https://hbr.org/2019/02/the-value-of-mentoring

Guide to Conducting a Personal SWAT Analysis

https://bschool.pepperdine.edu/blog/posts/personal-swot-analysis-guide.htm

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

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

Add These Growth Oriented Books

Are you ready to add some growth oriented books to your reading list? About this time of year I post up a list of the books I have read in the prior year. Other leaders and personalities post of lists of books and articles that they have taken advantage of such as Ryan Holiday, Tim Ferris, and Oprah. My list is now in it’s third year, and it is just as unique and interesting as the prior years.

What’s new this year over prior lists?

The list this year includes some more fiction to help me increase creativity. Imagination is like a muscle that expands when you use it. Furthermore, I’m starting to go for more seminal works that are more in depth and less books that I would categorize as “popular non-fiction.”

Peaks and Valleys

One thing I have learned more about myself this year by looking back on the prior 3 years is that there are periods of time where I get more reading done. Then, there are the times I get less done. For some reason December, January, and February are very productive months for me annually. All of this makes me wonder if others notice a specific time of year where reading increases or decreases. Let me know.

Stack of Books at Home for Growth Orientation

The Listings

Without further ado, please take a look at my latest book list for growth oriented leaders below. Additionally, if you want to see the prior lists head to my posts entitled Increase Your Quality Inputs and Readers are Leaders.

Growth Oriented Books for Your Reading List:

  • Setting the Table by Danny Meyer
  • Smart Brevity by Jim Vande Hei, Mark Allen, and Roy Schwartz
  • Setting the Table by Danny Meyer 
  • You are a Bad Ass by Jen Sincero
  • Flourish by Martin Seligman
  • Go for No by Richard Fenton and Andrea Waltz
  • As a Man Thinketh by James Allen
  • The Science of Getting Rich by Wallace Wattles
  • A Desolation Called Peace by Arkady Martine
  • The Four Agreements by Don Miguel Ruiz Don Jose Ruiz
  • The Games People Play by Eric Berne
  • The Creature from Jekyll by G. Edward Griffin
  • The Art of Possibility by Rosamund and Benjamin Zander
  • Influence, New and Expanded by Robert Cialdini 
  • Excellent Advice for Living: Wisdom I Wish I’d Known Earlier by Kevin Kelly
  • From Conflict to Courage by Marlene Chism
  • How to Win Friends and Influence People by Dale Carnegie
  • Great CEOs Are Lazy by Jim Schleckser
  • Civil War Stories by Ambrose Bierce 
  • Book Yourself Solid by Michael Port
  • Unwind! 7 Principles for a Stress-Free Life by Michael Olpin & Sam Bracken
  • 21 Success Secrets of Self Made Millionaires by Brian Tracy
  • Titan by Ron Chernow
  • Stillness is the Key by Ryan Holiday
  • Guns, Germs, and Steel by Jared Diamond 
  • Breaking the Habit of Being Yourself by Joe Dispenza
  • In My Own Way – Alan Watts
  • Mastery by Robert Greene
  • Business Secrets of Trappist Monks by August Turak
  • Your Next Five Moves: Master The Art of Business Strategy by Patrick Bet-David
  • Questions are the Answer – Hal Gregerson
  • The Confident Mind by Nate Zinsser

Hopefully this list of growth oriented books serves you well.

My Growth Oriented Books

While you are thinking about reading head over to my books page for growth oreinted books that I wrote in 2023. They are short reads but packed with knowledge and actionable insights. Head to the My Books page now to learn more.

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

Increase Your Quality Inputs

As I previously wrote, Readers are Leaders, I have really tried to dramatically increase quality and quantity of my book consumption. It has worked. I’ve gone from 10-20 books in 2019 to 30-40 a year (past 12 months). My ideal target is 52 plus — 1 book a week. This year I did a few more than last, but also wrote a book (more on that later), so I’m pretty happy with the effort.

Without more delay, here is a list of most of the books I have read in the past year.  Most of them were recommended to me and now I recommend them to you. If you ever want specific book recommendations please reach out.

  • Sons of Wichita by Daniel Schulman
  • What Makes Sammy Run? By Budd Schulberg
  • Never Finished by David Goggins
  • Onassis by Frank Brady
  • You2 by Price Prichett
  • Finding Mezcal by Ron Cooper
  • Atomic Habits by James Clear
  • $100M Offers by Alex Hormozi
  • Abundance by Steve Kotler and Peter Diamondis 
  • We Should All Be Millionaires by Rachel Rogers
  • Dopamine Nation by Anna Lembke
  • William Tecumseh Sherman by James Lee McDonough
  • Unshakable by Tony Robbins
  • Courage is Calling by Ryan Holiday
  • The Almanack of Naval Ravikant by Eric Jorgenson
  • Contagious by Jonah Berger
  • The Inevitable: Understanding the 12 Technological Forces that will Shape Our Future by Kevin Kelly 
  • Essentialism by Greg McKeown
  • 10x Rule by Grant Cardone
  • Raise Your Healthy Deserve Level by Gary Kadi
  • Coaching for Performance by Sir John Whitmore
  • Peak (New Science of Expertise) by Anders Ericsson and Robert Pool
  • So Good They Can’t Ignore You by Cal Newport
  • Build by Tony Fadell
  • Dare to Lead by Beene Brown
  • The Antidote: Happiness for People who can’t stand positive thinking by Oliver Burkeman 
  • Guerrilla Marketing for Coaches by Jay Conrad Levinson and Andrew Neitlich
  • Art of Gathering by Priya Parker
  • Greenlights by Mathew McConaughey
  • High Performance Habits by Brendon Burchard
  • Business of Belonging by David Spinks 
  • Originals by Adam Grant

An Invitation

Deep down we all know that we can be more, much more.

There is a future picture of ourselves in each of us that is much bigger and more exciting than where we are now. But are we ready to take the courageous path to become that new version of ourselves?

“Wanting what you want” is not only about being free and living life based on great choices and new commitments, it is also about painting a much, much bigger picture for yourself and those you lead, while also getting on the right path that looks scary and full of unknowns.

Most of us are avoiding the courageous pathway to get us to that bigger future. What we are each missing is an invitation to become courageous — to become a new version of ourselves. Sadly, most will never get that invitation. But now I am extending that invitation to you. I’d like to invite you to take the remainder of this year to be much more so that you can swing through to a transformational 2023. I want you to be intellectually excited and emotionally committed to that new big future.

If you are reading this post, please know that I believe in you, perhaps more than you believe in yourself. As a result, I want you to dream of a bigger future for yourself and remember that in life you don’t get what you deserve. You get what you think you deserve. You need to have courage to want what you want and at the same time eliminate lesser goals that are distracting you. I invite you to dream and take the right kind of risks that play to your distinctive strengths and discovery a bigger present.

Keep dreaming because when your future gets bigger, your present gets better.

You Can’t Give Something You Don’t Have

It’s hard to learn how to live and lead [a great life] while you are living, let alone consider leaving a legacy.

You know deep down you can be more . . . We all feel that way.  We want to be more so that we have more to give.

And we want to become more in many dimensions of life, because a life can be unlived in so many ways.

What we are each missing is an invitation to take a courageous path.  

And sadly most will never get that invitation.

I’m extending that invitation to you. Build your life, leadership, and legacy, because you can’t give something you don’t have.

Reach out to me anytime to learn more. If you have gotten this far, let’s talk for 30 minutes about life, leadership, and legacy. Let’s talk about your future and how coaching gets you there faster and how it is different than anything else you may have encountered.