Are you an idiot at fundraising?

Humans undervalue what they don't grasp. Consider NASCAR. How is that a sport? ask uneducated observers. Circular traffic. Driving near a car's physical limits is different from daily driving. When driving at 200 mph, seemingly simple things like changing gas weight or asphalt temperature might be life-or-death.

Venture investors do something similar in entrepreneurship. Most entrepreneurs don't realize how complex venture finance is.

In my early startup days, I didn't comprehend venture capital's intricacy. I thought VCs were rich folks looking for the next Mark Zuckerberg. I was meant to be a sleek, enthusiastic young entrepreneur who could razzle-dazzle investors.

Finally, one of the VCs I was trying to woo set me straight. He insulted me.

How I learned that I was approaching the wrong investor

I was constructing a consumer-facing, pre-revenue marketplace firm. I looked for investors in my old university's alumni database. My city had one. After some research, I learned he was a partner at a growth-stage, energy-focused VC company with billions under management.

Billions? I thought. Surely he can write a million-dollar cheque. He'd hardly notice.

I emailed the VC about our shared alumni status, explaining that I was building a startup in the area and wanted advice. When he agreed to meet the next week, I prepared my pitch deck.

First error.

The meeting seemed like a funding request. Imagine the awkwardness.

His assistant walked me to the firm's conference room and told me her boss was running late. While waiting, I prepared my pitch. I connected my computer to the projector, queued up my PowerPoint slides, and waited for the VC.

He didn't say hello or apologize when he entered a few minutes later. What are you doing?

Hi! I said, Confused but confident. Dinin Aaron. My startup's pitch.

Who? Suspicious, he replied. Your email says otherwise. You wanted help.

I said, "Isn't that a euphemism for contacting investors?" Fundraising I figured I should pitch you.

As he sat down, he smiled and said, "Put away your computer." You need to study venture capital.

Recognizing the business aspects of venture capital

The VC taught me venture capital in an hour. Young entrepreneur me needed this lesson. I assume you need it, so I'm sharing it.

Most people view venture money from an entrepreneur's perspective, he said. They envision a world where venture capital serves entrepreneurs and startups.

As my VC indicated, VCs perceive their work differently. Venture investors don't serve entrepreneurs. Instead, they run businesses. Their product doesn't look like most products. Instead, the VCs you're proposing have recognized an undervalued market segment. By investing in undervalued companies, they hope to profit. It's their investment thesis.

Your company doesn't fit my investment thesis, the venture capitalist told me. Your pitch won't beat my investing theory. I invest in multimillion-dollar clean energy companies. Asking me to invest in you is like ordering a breakfast burrito at a fancy steakhouse. They could, but why? They don't do that.

Yeah, I’m not a fine steak yet, I laughed, feeling like a fool for pitching a growth-stage VC used to looking at energy businesses with millions in revenues on my pre-revenue, consumer startup.

He stressed that it's not necessary. There are investors targeting your company. Not me. Find investors and pitch them.

Remember this when fundraising. Your investors aren't philanthropists who want to help entrepreneurs realize their company goals. Venture capital is a sophisticated investment strategy, and VC firm managers are industry experts. They're looking for companies that meet their investment criteria. As a young entrepreneur, I didn't grasp this, which is why I struggled to raise money. In retrospect, I probably seemed like an idiot. Hopefully, you won't after reading this.

New ventures are exciting. It's fun to imagine yourself rich, successful, and famous (if that's your thing). How you'll help others and make your family proud. This excitement can pull you forward for years, even when you intuitively realize that the path you're on may not lead to your desired success.

Know when to change course. Switching course can mean pivoting or changing direction.

In this not-so-short blog, I'll describe the journey of building your dream. And how the journey might look when you think you're building your dream, but fall short of that vision. Both can feel similar in the beginning, but there are subtle differences.

Let’s dive in.

How an exciting journey to a dead end looks and feels.

You want to help many people. You're business-minded, creative, and ambitious. You jump into entrepreneurship. You're excited, free, and in control.

I'll use tech as an example because that's what I know best, but this applies to any entrepreneurial endeavor.

So you start learning the basics of your field, say coding/software development. You read books, take courses, and may even join a bootcamp. You start practicing, and the journey begins. Once you reach a certain level of skill (which can take months, usually 12-24), you gain the confidence to speak with others in the field and find common ground. You might attract a co-founder this way with time. You and this person embark on a journey (Tip: the idea you start with is rarely the idea you end with).

Amateur mistake #1: You spend months building a product before speaking to customers.

Building something pulls you forward blindly. You make mistakes, avoid customers, and build with your co-founder or small team in the dark for months, usually 6-12 months.

You're excited when the product launches. We'll be billionaires! The market won't believe it. This excites you and the team. Launch.

….

Nothing happens.

Some people may sign up out of pity, only to never use the product or service again.

You and the team are confused, discouraged and in denial. They don't get what we've built yet. We need to market it better, we need to talk to more investors, someone will understand our vision.

This is a hopeless path, and your denial could last another 6 months. If you're lucky, while talking to consumers and investors (which you should have done from the start), someone who has been there before would pity you and give you an idea to pivot into that can create income.

Suppose you get this idea and pivot your business. Again, you've just pivoted into something limited by what you've already built. It may be a revenue-generating idea, but it's rarely new. Now you're playing catch-up, doing something others are doing but you can do better. (Tip #2: Don't be late.) Your chances of winning are slim, and you'll likely never catch up.

You're finally seeing revenue and feel successful. You can compete, but if you're not a first mover, you won't earn enough over time. You'll get by or work harder than ever to earn what a skilled trade could provide. You didn't go into business to stress out and make $100,000 or $200,000 a year. When you can make the same amount by becoming a great software developer, electrician, etc.

You become stuck. Either your firm continues this way for years until you realize there isn't enough growth to recruit a strong team and remove yourself from day-to-day operations due to competition. Or a catastrophic economic event forces you to admit that what you were building wasn't new and unique and wouldn't get you where you wanted to be.

This realization could take 6-10 years. No kidding.

The good news is, you’ve learned a lot along the way and this information can be used towards your next venture (if you have the energy).

Key Lesson: Don’t build something if you aren’t one of the first in the space building it just for the sake of building something.

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Let's discuss what it's like to build something that can make your dream come true.

Case 2: Building something the market loves is difficult but rewarding.

It starts with a problem that hasn't been adequately solved for a long time but is now solvable due to technology. Or a new problem due to a change in how things are done.

Let's examine each example.

Example #1: Mass communication. The problem is now solvable due to some technological breakthrough.

Twitter — One of the first web 2 companies that became successful with the rise of smart mobile computing.

People can share their real-time activities via mobile device with friends, family, and strangers. Web 2 and smartphones made it easy and fun.

Example #2: A new problem has emerged due to some change in the way things are conducted.

Zoom- A web-conferencing company that reached massive success due to the movement towards “work from home”, remote/hybrid work forces.

Online web conferencing allows for face-to-face communication.

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These two examples show how to build a unicorn-type company. It's a mix of solving the right problem at the right time, either through a technological breakthrough that opens up new opportunities or by fundamentally changing how people do things.

Let's find these opportunities.

Start by examining problems, such as how the world has changed and how we can help it adapt. It can also be both. Start team brainstorming. Research technologies, current world-trends, use common sense, and make a list. Then, choose the top 3 that you're most excited about and seem most workable based on your skillsets, values, and passion.

Once you have this list, create the simplest MVP you can and test it with customers. The prototype can be as simple as a picture or diagram of user flow and end-user value. No coding required. Market-test. Twitter's version 1 was simple. It was a web form that asked, "What are you doing?" Then publish it from your phone. A global status update, wherever you are. Currently, this company has a $50 billion market cap.

Here's their MVP screenshot.

Small things grow. Tiny. Simplify.

Remember Frequency and Value when brainstorming. Your product is high frequency (Twitter, Instagram, Snapchat, TikTok) or high value (Airbnb for renting travel accommodations), or both (Gmail).

Once you've identified product ideas that meet the above criteria, they're simple, have a high frequency of use, or provide deep value. You then bring it to market in the simplest, most cost-effective way. You can sell a half-working prototype with imagination and sales skills. You need just enough of a prototype to convey your vision to a user or customer.

With this, you can approach real people. This will do one of three things: give you a green light to continue on your vision as is, show you that there is no opportunity and people won't use it, or point you in a direction that is a blend of what you've come up with and what the customer / user really wants, and you update the prototype and go back to the maze. Repeat until you have enough yeses and conviction to build an MVP.

Believe what you see, what people say

It’s sad that we never get trained to leave assumptions behind. - Sebastian Thrun

Many problems in software development are not because of code but because developers create the wrong software. This isn't rare because software is emergent and most individuals only realize what they want after it's built.

Inquisitive developers who pass the yellow cat test can improve the process.

Carpenters measure twice and cut the wood once. Developers are rarely so careful.

The Yellow Cat Test

Game of Thrones made dragons cool again, so I am reading The Game of Thrones book.

The yellow cat exam is from Syrio Forel, Arya Stark's fencing instructor.

Syrio tells Arya he'll strike left when fencing. He hits her after she dodges left. Arya says “you lied”. Syrio says his words lied, but his eyes and arm told the truth.

Arya learns how Syrio became Bravos' first sword.

“On the day I am speaking of, the first sword was newly dead, and the Sealord sent for me. Many bravos had come to him, and as many had been sent away, none could say why. When I came into his presence, he was seated, and in his lap was a fat yellow cat. He told me that one of his captains had brought the beast to him, from an island beyond the sunrise. ‘Have you ever seen her like?’ he asked of me.

“And to him I said, ‘Each night in the alleys of Braavos I see a thousand like him,’ and the Sealord laughed, and that day I was named the first sword.”

Arya screwed up her face. “I don’t understand.”

Syrio clicked his teeth together. “The cat was an ordinary cat, no more. The others expected a fabulous beast, so that is what they saw. How large it was, they said. It was no larger than any other cat, only fat from indolence, for the Sealord fed it from his own table. What curious small ears, they said. Its ears had been chewed away in kitten fights. And it was plainly a tomcat, yet the Sealord said ‘her,’ and that is what the others saw. Are you hearing?” Reddit discussion.

Development teams should not believe what they are told.

We created an appointment booking system. We thought it was an appointment-booking system. Later, we realized the software's purpose was to book the right people for appointments and discourage the unneeded ones.

The first 3 months of the project had half-correct requirements and software understanding.

Open your eyes

“Open your eyes is all that is needed. The heart lies and the head plays tricks with us, but the eyes see true. Look with your eyes, hear with your ears. Taste with your mouth. Smell with your nose. Feel with your skin. Then comes the thinking afterwards, and in that way, knowing the truth” Syrio Ferel

We must see what exists, not what individuals tell the development team or how developers think the software should work. Initial criteria cover 50/70% and change.

Developers build assumptions problems by assuming how software should work. Developers must quickly explain assumptions.

When a development team's assumptions are inaccurate, they must alter the code, DevOps, documentation, and tests.

It’s always faster and easier to fix requirements before code is written.

First-draft requirements can be based on old software. Development teams must grasp corporate goals and consider needs from many angles.

Testers help rethink requirements. They look at how software requirements shouldn't operate.

Technical features and benefits might misdirect software projects.

The initiatives that focused on technological possibilities developed hard-to-use software that needed extensive rewriting following user testing.

Software development

High-level criteria are different from detailed ones.

• The interpretation of words determines their meaning.

• Presentations are lofty, upbeat, and prejudiced.

• People's perceptions may be unclear, incorrect, or just based on one perspective (half the story)

• Developers can be misled by requirements, circumstances, people, plans, diagrams, designs, documentation, and many other things.

Developers receive misinformation, misunderstandings, and wrong assumptions. The development team must avoid building software with erroneous specifications.

Once code and software are written, the development team changes and fixes them.

Developers create software with incomplete information, they need to fill in the blanks to create the complete picture.

Conclusion

Yellow cats are often inaccurate when communicating requirements.

Before writing code, clarify requirements, assumptions, etc.

Everyone will pressure the development team to generate code rapidly, but this will slow down development.

Code changes are harder than requirements.