Leadership and Fundraising:
A Foundation for Success
From career to startup CEO — what it really takes to make the leap and raise your first round.
What you’ll learn
In these courses, I share my journey from computer science professor to serial entrepreneur, detailing how I transitioned from a technical leader into the role of startup CEO. Along the way, I unpack the hard-earned lessons from my first time leading a company, the dynamics of building founding teams, and the realities of navigating early-stage financing. Drawing on my experience across nine startups, I explain what founders can expect—from friends-and-family rounds through venture capital—and the critical mistakes to avoid at each stage.
With the experience of guiding hundreds of founders through the treacherous early phases where most startups falter, I designed these foundational courses to help you build confidence and clarity. You’ll learn how to overcome imposter syndrome, establish your leadership presence, and master the fundraising process that trips up so many first-time CEOs. I’ll walk you through my battle-tested pitching framework that secured millions in funding, show you how to identify the right investors while steering clear of toxic ones, and teach you how to navigate due diligence like a pro. By the end, you’ll be equipped to approach investors with the confidence and credibility of a seasoned founder.
Ready to transform your fundraising approach? Buy all Leadership & Fundraising Courses and save!
Leadership & Fundraising Courses:
This free introductory module gives founders a grounded starting point before they dive into the deeper mechanics of leading a company or raising capital. It frames the journey ahead by highlighting the mindset, motivations, and early decisions that shape a founder’s trajectory. Drawing on Jothy Rosenberg’s experience building nine startups, the module offers an honest look at what truly underpins effective leadership and fundraising long before pitch decks or investor meetings come into play.
Free lessons: • Introduction • Entrepreneurial mindset • Scratching the startup itch
Free resource: Entrepreneurial Mindset Self-Assessment
The CEO Readiness module tackles the make-or-break question every founding team faces: who should lead—and are they truly prepared? Across three focused lessons, founders learn to silence imposter syndrome and step confidently into the CEO seat, identify the most common first-time CEO pitfalls and red flags before they become costly, and hear Jothy Rosenberg's own unvarnished story of leading a company for the first time—what worked, what didn't, and what he wishes he'd known.
Lessons included: • Who Should Be CEO — Overcoming Imposter Syndrome • First-Time CEO — Key Challenges & Red Flags • First-Time CEO — My Story
Before chasing funding or writing code, every founder needs to understand what it truly means to start a company—and what happens when founders lose their way. This module distills the essential DNA of successful founders: what drives them, what distinguishes the great ones, and the patterns that predict trouble. Through vivid real-world cautionary tales, founders learn to recognize the warning signs of ego, misalignment, and unchecked behavior before they derail a venture.
Lessons included: • All About Founders • Founders Gone Rogue — A Few Horror Stories to Keep in Mind
Raising money is where most first-time founders stumble—not because good ideas lack capital, but because they don't understand how startup funding actually works. This module walks founders through the fundraising landscape from day one: the different rounds and what each demands, how to structure a friends-and-family raise without destroying relationships, the art and mechanics of pitching investors and closing commitments, and when and how to leverage angel investors for maximum impact. Founders finish with a clear, stage-appropriate fundraising strategy they can execute immediately.
Lessons included: • Different Funding Rounds for Startups • A Friends and Family Raise • Pitching to Investors — And Securing Funding • All About Angels — When to Use Them and How to Raise from Them
Understanding how investors actually think is one of the most underrated advantages a founder can have. This module pulls back the curtain on the investor–founder relationship: why treating investors as friends is a dangerous mistake, how misaligned incentives create blind spots, and what really drives institutional investor decision-making. Founders learn to decode the mental models, risk frameworks, and portfolio logic that VCs and institutional investors use—so they can walk into any meeting prepared to speak the investor's language and negotiate from strength.
Lessons included: • Investors Are Not Your Friend — Why This Is Important • How Institutional Investors Tick — It Helps to Think Like Them
The seed round is the moment a startup goes from scrappy experiment to funded company—and getting it wrong can set founders back years. This module breaks down exactly how to raise a seed round as the first priced equity round: what investors expect, how to structure the raise, and what "priced round" really means for ownership and control. Founders also get a plain-language deep dive into term sheets—what every clause means, when to expect one, and how to negotiate terms that protect the company's future without scaring off capital.
Lessons included: • Raising a Seed Round — The First Priced Round • Term Sheet — What Is It and When Should You Expect One?
Once an investor says "we're interested," the real test begins. Due diligence is the high-stakes exam every startup must pass before a check is written—and most founders walk in underprepared. This module demystifies the process in two parts: first, what investors are actually scrutinizing, how to anticipate tough questions, and what red flags will kill a deal; then, the practical mechanics of building a best-in-class data room that signals professionalism, transparency, and operational readiness. Founders who nail due diligence don't just close rounds—they close them faster and on better terms.
Lessons included: • Due Diligence Part 1 — It's an Exam You Have to Pass • Due Diligence Part 2 — Setting Up a Great Data Room
The Leadership & Fundraising module concludes by reinforcing the idea that effective leadership and successful fundraising are not isolated skills — they are deeply interconnected disciplines that shape a founder’s ability to guide a company through uncertainty, growth, and investor scrutiny. By the end, founders gain a clearer understanding of what it truly means to lead with confidence while navigating the realities of raising capital.
Free lesson: • Key learnings and next steps
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