Early-Stage Fundraising & Deal Structure (S5E6)


Fundraising and deal structure for early-stage companies are no joke. Actually, scratch that—this stuff is crucial for businesses of any size. Brace yourselves, because each contestant is about to face a figurative (who knows, maybe even literal in the future) gauntlet. They’re diving headfirst into the nitty-gritty of structuring a potential deal for their own company. And let me tell you, this Blox-Off is a relentless battle. The judges are leaving no stone unturned and no detail unnoticed. It’s a fierce showdown where every decision matters, and no slip-up goes unnoticed. Get ready for an epic finale like no other!


Our final day opens around the breakfast table with some serious reflection from judge Steven. This is the last chance for our determined entrepreneurs to pluck that juicy fruit from the tree of education, as Steven so eloquently puts it. It’s a moment of somber reflection that reminds us all that even the best entrepreneurs have room to grow. Fostering that growth and striving for improvement begins with intentional decision-making.

Now, let’s talk about investing in ourselves and diving into today’s topic: early-stage fundraising and deal structures. If there’s one skill that can make or break your company, it’s the ability to strike those all-important deals as you navigate the journey of growth. It’s also one of the fastest ways to crash and burn if you screw it up. Let’s learn from the class today and avoid that pain!

During the class, Wes drops some serious knowledge bombs on fundraising, money, and where the real power lies. We all know money plays a crucial role, but it’s just one piece of the puzzle when it comes to bartering and trading goods or services. Some of these goods or services can carry hefty price tags, like mobile applications, equipment, or the invaluable time and expertise of another person. Perhaps we can get creative and explore alternative deal structures. That’s the name of the game – get creative.

But hold on tight, because today’s exercise is throwing everyone off balance. The contestants are getting a bit too comfortable with the usual format, so it’s time to hit them with a classic pop-quiz curveball. Here’s how it goes: step outside, receive absolutely zero information, let fear creep in, return one by one, and brace yourselves for an intense pop-quiz from your judge. Each contestant has a mere 30 seconds to answer each question, and if they dare go over even by a single second, the pod directors have been granted extreme authority to shut it down.

Wes doesn’t hold back on this final day, my friends. The pod winners are immediately whisked off the stage without a moment’s notice, and the first contestant is thrust into the hot seat right away. They have a mere two minutes to create an investment pitch, with each judge assuming a different scenario. The judges will reveal who they are, what they do, their risk appetite, and more, all in an effort to guide the contestant. After that, it’s all up to the contestant to craft an ironclad deal structure that wins over the judges, convinces them to invest, and presents a fair and enticing opportunity.

Get ready for an electrifying finale, folks, because the stakes are high and every second counts. It’s a battle of wit, strategy, and negotiation skills that will determine who comes out on top. The tension is palpable, and the thrill of victory is within reach. Who will secure that coveted win? Stay tuned to find out!


Alright, let’s dive into the importance of fundraising and deal structure for early-stage companies. Buckle up, because this is where the rubber meets the road and the fate of your business hangs in the balance. Whether you’re a budding startup or a growing enterprise, mastering the art of making deals can make or break your company’s trajectory.

Think of it this way: every deal you make has the power to shape the trajectory of your company. It’s not just about the immediate financial gains but also about the long-term impact and relationships forged along the way. Crafting solid deal structures requires careful consideration of the value exchange, the potential risks, and the overall alignment with your business objectives. It’s about being creative, nimble, and seizing opportunities that align with your vision.


  1. Know your business stage before making deals. We delve into them during the class: aspiring entrepreneur, idea stage, building/testing/tweaking, product-market fit, growth, liquidation, and corporation stages.
  2. In every city, a treasure trove of resources awaits founders at every stage. It’s on you to uncover the supportive gears of your local startup ecosystem. Research, explore, and seize the opportunities available to propel your journey forward.
  3. Fundraising success hinges on timing, not just who or what you are. Community events barely affect growth and liquidation stages. Likewise, venture capitalists and angel investors show little interest in aspiring entrepreneurs or idea stage companies. Timing is everything!
  4. Entrepreneurial fundraising follows a similar pattern. The capital you can raise aligns with your actual stage. Your traction determines the type/stage. No pitch or idea alone can secure VC dollars for pre-revenue entrepreneurs (unless they have an exit or fame). Traction speaks volumes!
  5. Financing deal structure goes beyond what Shark Tank portrays. For instance, giving equity to a friend when they desired a quick loan is quasi-fraudulent. Conversely, providing a loan structure when they wanted to take a bold bet misrepresents their intentions. It’s an art!
  6. Cracking the code of early-stage financing with investors, especially family, requires understanding their motivations. Once you’ve grasped their driving forces, the key lies in aligning their aspirations with the appropriate deal structure. It’s all about finding the perfect match!

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Meet The Judges

Darwin Liu
Darwin Liu
Founder, CEO of X Agency

Darwin Liu is the founder and CEO of X Agency. He believes in the power of strategic digital marketing and always finding the most efficient way to work with clients’ budgets and grow their revenue. He cut his teeth as an entry-level account manager at a large agency and quickly rose through the ranks to become the fastest promoted at the agency. He managed digital strategy for the largest accounts which totaled over $50M in annual spending. Throughout this time, Darwin established himself as a thought leader in the industry. In June 2017, he followed his entrepreneurial desires and founded X Agency. Darwin always has his eye focused on growing X Agency consistently hitting milestones since its founding.

John Rake
John Rake
CTO BetaBlox, CEO BuildingBlox

John’s passion lies in helping entrepreneurs and startup founders launch amazing software into the market that customers love. He partners with early-stage companies, to help them validate their ideas, to build software that matters and that customers actually want to buy. John has helped many bold entrepreneurs solve big problems that create a lasting impact.

Kaitlyn Lemus Portillo
Kaitlyn Lemus Portillo
Owner, Money Mindset & Magic Mastermind, Freedom Automations

Kaitlyn has been leveraging her expertise to help companies create structure around their ideas and scale their businesses for over a decade. In her signature program Money Mindset & Magic, she and her team coach entrepreneurs on how to create systems that support growth at their unique starting point. She is known for her raw, authentic coaching style and encouraging her clients to connect to their authentic selves so they can elevate at exponential rates. After signing her first major publishing deal with Universal Music Publishing, Kaitlyn’s work was featured on Disney’s “A Cinderella Story”, Rebecca Black (It’s Friday!), as well as HGTV shows.

Matt Shatto
Matt Shatto
Founder, CEO Shatto Milk

Matt Shatto, the innovative CEO of Shatto Milk, has achieved remarkable success in the dairy industry. Hailing from Kansas City, Missouri, Matt’s entrepreneurial journey is a testament to his unwavering commitment to quality and innovation. Through his leadership, Shatto Milk has become a beloved brand known for its farm-fresh, handcrafted milk. Matt’s ability to navigate the challenges of the industry and his dedication to local, sustainable farming have earned him a well-deserved reputation as a pioneering entrepreneur. With his Midwestern charm and genuine passion for his craft, Matt continues to delight customers and redefine the dairy experience.

Nemanja "Neman" Golubovic
Nemanja "Neman" Golubovic
Founder, CEO of Kale My Name

Nemanja Golubovic, an entrepreneur from Montenegro, is the CEO and Founder of Kale My Name, one of America’s most successful vegan restaurants. Upon its launch, his mission has been to transform how people eat by providing plant-based meals that contribute to human health and look after our planet. With few resources and opportunities available to him when he first arrived in the United States from Montenegro, Golubovic has worked hard to become a successful business owner and provide healthy options for those who want them.

Steven Khuong
Steven Khuong
Co-founder, CEO at Curacubby, Inc.

Steven is the co-founder and CEO of Curacubby, a Next-Gen Fintech platform for education, recreation, and family activity programs. As a thought leader in operations and process management, Steven has been featured in international media including CNN, Forbes.com, and Inc. Magazine. He currently serves as a mentor at the Envestnet | Yodlee Fintech Launchpad, as an advisor to the Arrowhead Center of Innovation at New Mexico State University, and previously a parent co-founder of an early education program for children with special needs.

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