A top-down company plan facilitates decision-making and impresses investors.

A startup business plan starts with the product, the target customers, how to reach them, and how to grow the business.

Bottom-up is terrific unless venture investors fund it.

If it can prove how it can exceed $100M in sales, investors will invest. If not, the business may be wonderful, but it's not venture capital-investable.

As a rule, venture investors only fund firms that expect to reach $100M within 5 years.

Investors get nothing until an acquisition or IPO. To make up for 90% of failed investments and still generate 20% annual returns, portfolio successes must exit with a 25x return. A $20M-valued company must be acquired for $500M or more.

This requires $100M in sales (or being on a nearly vertical trajectory to get there). The company has 5 years to attain that milestone and create the requisite ROI.

This motivates venture investors (venture funds and angel investors) to hunt for $100M firms within 5 years. When you pitch investors, you outline how you'll achieve that aim.

I'm wary of pitches after seeing a million hockey sticks predicting $5M to $100M in year 5 that never materialized. Doubtful.

Startups fail because they don't have enough clients, not because they don't produce a great product. That jump from $5M to $100M never happens. The company reaches $5M or $10M, growing at 10% or 20% per year.  That's great, but not enough for a $500 million deal.

Once it becomes clear the company won’t reach orbit, investors write it off as a loss. When a corporation runs out of money, it's shut down or sold in a fire sale. The company can survive if expenses are trimmed to match revenues, but investors lose everything.

When I hear a pitch, I'm not looking for bright income projections but a viable plan to achieve them. Answer these questions in your pitch.

• Is the market size sufficient to generate $100 million in revenue?

• Will the initial beachhead market serve as a springboard to the larger market or as quicksand that hinders progress?

• What marketing plan will bring in $100 million in revenue? Is the market diffuse and will cost millions of dollars in advertising, or is it one, focused market that can be tackled with a team of salespeople?

• Will the business be able to bridge the gap from a small but fervent set of early adopters to a larger user base and avoid lock-in with their current solution?

• Will the team be able to manage a $100 million company with hundreds of people, or will hypergrowth force the organization to collapse into chaos?

• Once the company starts stealing market share from the industry giants, how will it deter copycats?

The requirement to reach $100M may be onerous, but it provides a context for difficult decisions: What should the product be? Where should we concentrate? who should we hire? Every strategic choice must consider how to reach $100M in 5 years.

Focusing on $100M streamlines investor pitches. Instead of explaining everything, focus on how you'll attain $100M.

As an investor, I know I'll lose my money if the startup doesn't reach this milestone, so the revenue prediction is the first thing I look at in a pitch deck.

Reaching the $100M goal needs to be the first thing the entrepreneur thinks about when putting together the business plan, the central story of the pitch, and the criteria for every important decision the company makes.

I pitched 10 brands per workday for a total of 200.

How did I do?

It was difficult.

I've never pitched so much.

What did this challenge teach me?

• the superiority of quality over quantity

• When you need help, outsource

• Don't disregard burnout in order to complete a challenge because it exists.

First, pitching brands for brand deals requires quality. Find firms that align with your brand to expose to your audience.

If you associate with any company, you'll lose audience loyalty. I didn't lose sight of that, but I couldn't resist finishing the task.

Outsourcing.

Delegating work to teammates is effective.

I wish I'd done it.

Three people can pitch 200 companies a month significantly faster than one.

One person does research, one to two do outreach, and one to two do follow-up and negotiating.

Simple.

In 2022, I'll outsource everything.

Burnout.

I felt this, so I slowed down at the end of the month.

Thanksgiving week in November was slow.

I was buying and decorating for Christmas. First time putting up outdoor holiday lights was fun.

Much was happening.

I'm not perfect.

I'm being honest.

The Outcomes

Less than 50 brands pitched.

Result: A deal with 3 brands.

I hoped for 4 brands with reaching out to 200 companies, so three with under 50 is wonderful.

That’s a 6% conversion rate!

Whoo-hoo!

I needed 2%.

Here's a screenshot from one of the deals I booked.

These companies fit my company well. Each campaign is different, but I've booked $2,450 in brand work with a couple of pending transactions for December and January.

$2,450 in brand work booked!

How did I do? You tell me.

Is this something you’d try yourself?

We love round numbers, don't we? $100,000 is a frequent freelancing milestone. You feel like six figures means you're doing something properly.

You've most likely already conquered initial freelancing challenges like finding clients, setting fair pricing, coping with criticism, getting through dry spells, managing funds, etc.

You think I must be doing well. Last month, my freelance income topped $100,000.

That may not sound impressive considering I've been freelancing for 2.75 years, but I made 30% of that in the previous four months, which is crazy.

Here are the things I wish I'd known during the early days of self-employment that would have helped me hit $100,000 faster.

1. The Volatility of Freelancing Will Stabilize.

Freelancing is risky. No surprise.

Here's an example.

October 2020 was my best month, earning $7,150. Between $4,004 in September and $1,730 in November. Unsteady.

Freelancing is regrettably like that. Moving clients. Content requirements change. Allocating so much time to personal pursuits wasn't smart, but yet.

Stabilizing income takes time. Consider my rolling three-month average income since I started freelancing. My three-month average monthly income. In February, this metric topped $5,000. Now, it's in the mid-$7,000s, but it took a while to get there.

Finding freelance gigs that provide high pay, high volume, and recurring revenue is difficult. But it's not impossible.

TLDR: Don't expect a steady income increase at first. Be patient.

2. You Have More Value Than You Realize.

Writing is difficult. Assembling words, communicating a message, and provoking action are a puzzle.

People are willing to pay you for it because they can't do what you do or don't have enough time.

Keeping that in mind can have huge commercial repercussions.

When talking to clients, don't tiptoe. You can ignore ridiculous deadlines. You don't have to take unmanageable work.

You solve an issue, so make sure you get rightly paid.

TLDR: Frame services as problem-solutions. This will let you charge more and set boundaries.

3. Increase Your Prices.

I studied hard before freelancing. I read articles and watched videos about writing businesses.

I didn't want to work for pennies. Despite this clarity, I had no real strategy to raise my rates.

I then luckily stumbled into higher-paying work. We discussed fees and hours with a friend who launched a consulting business. It's subjective and speculative because value isn't standardized. One company may laugh at your charges. If your solution helps them create a solid ROI, another client may pay $200 per hour.

When he told me he charged his first client $125 per hour, I thought, Why not?

A new-ish client wanted to discuss a huge forthcoming project, so I raised my rates. They knew my worth, so they didn't blink when I handed them my new number.

TLDR: Increase rates periodically (e.g., every 6 or 12 months). Writing skill develops with practice. You'll gain value over time.

4. Remember Your Limits.

If you can squeeze additional time into a day, let me know. I can't manipulate time yet.

We all have time and economic limits. You could theoretically keep boosting rates, but your prospect pool diminishes. Outsourcing and establishing extra revenue sources might boost monthly revenues.

I've devoted a lot of time to side projects (hopefully extra cash sources), but I've only just started outsourcing. I wish I'd tried this earlier.

If you can discover good freelancers, you can grow your firm without sacrificing time.

TLDR: Expand your writing network immediately. You'll meet freelancers who understand your daily grind and locate reference sources.

5. Every Action You Take Involves an Investment. Be Certain to Select Correctly.

Investing in stocks or crypto requires paying money, right?

In business, time is your currency (and maybe money too). Your daily habits define your future. If you spend time collecting software customers and compiling content in the space, you'll end up with both. So be sure.

I only spend around 50% of my time on client work, therefore it's taken me nearly three years to earn $100,000. I spend the remainder of my time on personal projects including a freelance book, an investment newsletter, and this blog.

Why? I don't want to rely on client work forever. So, I'm working on projects that could pay off later and help me live a more fulfilling life.

TLDR: Consider the long-term impact of your time commitments, and don't overextend. You can only make so many "investments" in a given time.

6. LinkedIn Is an Endless Mine of Gold. Use It.

Why didn't I use LinkedIn earlier?

I designed a LinkedIn inbound lead strategy that generates 12 leads a month and a few high-quality offers. As a result, I've turned down good gigs. Wish I'd begun earlier.

If you want to create a freelance business, prioritize LinkedIn. Too many freelancers ignore this site, missing out on high-paying clients. Build your profile, post often, and interact.

TLDR: Study LinkedIn's top creators. Once you understand their audiences, start posting and participating daily.

For 99% of People, Freelancing is Not a Get-Rich-Quick Scheme.

Here's a list of things I wish I'd known when I started freelancing.

1. Although it is erratic, freelancing eventually becomes stable.

2. You deserve respect and discretion over how you conduct business because you have solved an issue.

3. Increase your charges rather than undervaluing yourself. If necessary, add a reminder to your calendar. Your worth grows with time.

4. In order to grow your firm, outsource jobs. After that, you can work on the things that are most important to you.

5. Take into account how your present time commitments may affect the future. It will assist in putting things into perspective and determining whether what you are doing is indeed worthwhile.

6. Participate on LinkedIn. You'll get better jobs as a result.

If I could give my old self (and other freelancers) one bit of advice, it's this:

Despite appearances, you're making progress.

Each job. Tweets. Newsletters. Progress. It's simpler to see retroactively than in the moment.

Consistent, intentional work pays off. No good comes from doing nothing. You must set goals, divide them into time-based targets, and then optimize your calendar.

Then you'll understand you're doing well.

Want to learn more? I’ll teach you.

Generative AI hype: some thoughts

The sudden surge in "generative AI" startups and projects feels like the inverse of the recent "web3" boom. Both came from hyped-up pots. But while web3 hyped idealistic tech and an easy way to make money, generative AI hypes unsettling tech and questions whether it can be used to make money.

Web3 is technology looking for problems to solve, while generative AI is technology creating almost too many solutions. Web3 has been evangelists trying to solve old problems with new technology. As Generative AI evolves, users are resolving old problems in stunning new ways.

It's a jab at web3, but it's true. Web3's hype, including crypto, was unhealthy. Always expected a tech crash and shakeout. Tech that won't look like "web3" but will enhance "web2"

But that doesn't mean AI hype is healthy. There'll be plenty of bullshit here, too. As moths to a flame, hype attracts charlatans. Again, the difference is the different starting point. People want to use it. Try it.

With the beta launch of Dall-E 2 earlier this year, a new class of consumer product took off. Midjourney followed suit (despite having to jump through the Discord server hoops). Twelve more generative art projects. Lensa, Prisma Labs' generative AI self-portrait project, may have topped the hype (a startup which has actually been going after this general space for quite a while). This week, ChatGPT went off-topic.

This has a "fake-it-till-you-make-it" vibe. We give these projects too much credit because they create easy illusions. This also unlocks new forms of creativity. And faith in new possibilities.

As a user, it's thrilling. We're just getting started. These projects are not only fun to play with, but each week brings a new breakthrough. As an investor, it's all happening so fast, with so much hype (and ethical and societal questions), that no one knows how it will turn out. Web3's demand won't be the issue. Too much demand may cause servers to melt down, sending costs soaring. Companies will try to mix rapidly evolving tech to meet user demand and create businesses. Frustratingly difficult.

Anyway, I wanted an excuse to post some Lensa selfies.

These are really weird. I recognize them as me or a version of me, but I have no memory of them being taken. It's surreal, out-of-body. Uncanny Valley.

From 1984 until 2011, he ran Apple using the same template.

What is a founder CEO's most crucial skill?

Presentation, communication, and sales

As a Business Angel Investor, I saw many pitch presentations and met with investors one-on-one to promote my companies.

There is always the conception of “Investors have to invest,” so there is no need to care about the presentation.

It's false. Nobody must invest. Many investors believe that entrepreneurs must convince them to invest in their business.

Sometimes — like in 2018–2022 — too much money enters the market, and everyone makes good money.

Do you recall the Buy Now, Pay Later Movement? This amazing narrative had no return potential. Only buyers who couldn't acquire financing elsewhere shopped at these companies.

Klarna's failing business concept led to high valuations.

Investors become more cautious when the economy falters. 2022 sees rising inflation, interest rates, wars, and civil instability. It's like the apocalypse's four horsemen have arrived.

Storytelling is important in rough economies.

When investors draw back, how can entrepreneurs stand out?

In Q2/2022, every study I've read said:

Investors cease investing

Deals are down in almost all IT industries from previous quarters.

What do founders need to do?

Differentiate yourself.

Storytelling talents help.

The Steve Jobs Way

Every time I watch a Steve Jobs presentation, I'm enthralled.

I'm a techie. Everything technical interests me. But, I skim most presentations.

What's Steve Jobs's secret?

Steve Jobs created Apple in 1976 and made it a profitable software and hardware firm in the 1980s. Macintosh goods couldn't beat IBM's. This mistake sacked him in 1985.

Before rejoining Apple in 1997, Steve Jobs founded Next Inc. and Pixar.

From then on, Apple became America's most valuable firm.

Steve Jobs understood people's needs. He said:

“People don’t know what they want until you show it to them. That’s why I never rely on market research. Our task is to read things that are not yet on the page.”

In his opinion, people talk about problems. A lot. Entrepreneurs must learn what the population's pressing problems are and create a solution.

Steve Jobs showed people what they needed before they realized it.

I'll explain:

Present a Big Vision

Steve Jobs starts every presentation by describing his long-term goals for Apple.

1984's Macintosh presentation set up David vs. Goliath. In a George Orwell-style dystopia, IBM computers were bad. It was 1984.

Apple will save the world, like Jedis.

Why do customers and investors like Big Vision?

People want a wider perspective, I think. Humans love improving the planet.

Apple users often cite emotional reasons for buying the brand.

Revolutionizing several industries with breakthrough inventions

Establish Authority

Everyone knows Apple in 2022. It's hard to find folks who confuse Apple with an apple around the world.

Apple wasn't as famous as it is today until Steve Jobs left in 2011.

Most entrepreneurs lack experience. They may market their company or items to folks who haven't heard of it.

Steve Jobs presented the company's historical accomplishments to overcome opposition.

In his presentation of the first iPhone, he talked about the Apple Macintosh, which altered the computing sector, and the iPod, which changed the music industry.

People who have never heard of Apple feel like they're seeing a winner. It raises expectations that the new product will be game-changing and must-have.

The Big Reveal

A pitch or product presentation always has something new.

Steve Jobs doesn't only demonstrate the product. I don't think he'd skip the major point of a company presentation.

He consistently discusses present market solutions, their faults, and a better consumer solution.

No solution exists yet.

It's a multi-faceted play:

• It's comparing the new product to something familiar. This makes novelty and the product more relatable.

• Describe a desirable solution.

• He's funny. He demonstrated an iPod with an 80s phone dial in his iPhone presentation.

Then he reveals the new product. Macintosh presented itself.

Show the benefits

He outlines what Apple is doing differently after demonstrating the product.

How do you distinguish from others? The Big Breakthrough Presentation.

A few hundred slides might list all benefits.

Everyone would fall asleep. Have you ever had similar presentations?

When the brain is overloaded with knowledge, the limbic system changes to other duties, like lunch planning.

What should a speaker do? There's a classic proverb:

“Tell me and I forget, teach me and I may remember, involve me and I learn” (— Not Benjamin Franklin).

Steve Jobs showcased the product live.

Again, using ordinary scenarios to highlight the product's benefits makes it relatable.

The 2010 iPad Presentation uses this technique.

Invite the Team and Let Them Run the Presentation

CEOs spend most time outside the organization. Many companies elect to have only one presenter.

It sends the incorrect message to investors. Product presentations should always include the whole team.

Let me explain why.

Companies needing investment money frequently have shaky business strategies or no product-market fit or robust corporate structure.

Investors solely bet on a team's ability to implement ideas and make a profit.

Early team involvement helps investors understand the company's drivers. Travel costs are worthwhile.

But why for product presentations?

Presenters of varied ages, genders, social backgrounds, and skillsets are relatable. CEOs want relatable products.

Some customers may not believe a white man's message. A black woman's message may be more accepted.

Make the story relatable when you have the best product that solves people's concerns.

Best example: 1984 Macintosh presentation with development team panel.

What is the largest error people make when companies fail?

Saving money on the corporate and product presentation.

Invite your team to five partner meetings when five investors are shortlisted.

Rehearse the presentation till it's natural. Let the team speak.

Successful presentations require structure, rehearsal, and a team. Steve Jobs nailed it.