What they'll do is scarier.

My acquaintance recently joined a VC-funded startup. Money, equity, and upside possibilities were nice, but he had a nagging dread.

They just secured a $40M round and are hiring like crazy to prepare for their IPO in two years. All signals pointed to this startup's (a B2B IT business in a stable industry) success, and its equity-holding workers wouldn't pass that up.

Five months after starting the work, my friend struggled with leaving. We might overlook the awful culture and long hours at the proper price. This price plus the company's fate and survival abilities sent my friend departing in an unpleasant unplanned resignation before jumping on yet another sinking ship.

This affects founders. This affects VC-backed companies (and all businesses). This affects anyone starting, buying, or running a business.

Here's the under-the-table approach that's draining VC capital, leaving staff terrified (or jobless), founders rattled, and investors upset. How to recognize, solve, and avoid it

The unsettling reality behind door #1

You can't raise money off just your looks, right? If "looks" means your founding team's expertise, then maybe. In my friend's case, the founding team's strong qualifications and track records won over investors before talking figures.

They're hardly the only startup to raise money without a profitable customer acquisition strategy. Another firm raised money for an expensive sleep product because it's eco-friendly. They were off to the races with a few keywords and key players.

Both companies, along with numerous others, elected to invest on product development first. Company A employed all the tech, then courted half their market (they’re a tech marketplace that connects two parties). Company B spent millions on R&D to create a palatable product, then flooded the world with marketing.

My friend is on Company B's financial team, and he's seen where they've gone wrong. It's terrible.

Company A (tech market): Growing? Not quite. To achieve the ambitious expansion they (and their investors) demand, they've poured much of their little capital into salespeople: Cold-calling commission and salary salesmen. Is it working? Considering attrition and companies' dwindling capital, I don't think so.

Company B (green sleep) has been hiring, digital marketing, and opening new stores like crazy. Growing expenses should result in growing revenues and a favorable return on investment; if you grow too rapidly, you may neglect to check that ROI.

Once Company A cut headcount and Company B declared “going concerned”, my friend realized both startups had the same ailment and didn't recognize it.

I shouldn't have to ask a friend to verify a company's cash reserves and profitability to spot a financial problem. It happened anyhow.

The frightening part isn't that investors were willing to invest millions without product-market fit, CAC, or LTV estimates. That's alarming, but not as scary as the fact that startups aren't understanding the problem until VC rounds have dried up.

When they question consultants if their company will be around in 6 months. It’s a red flag. How will they stretch $20M through a 2-year recession with a $3M/month burn rate and no profitability? Alarms go off.

Who's in danger?

In a word, everyone who raised money without a profitable client acquisition strategy or enough resources to ride out dry spells.

Money mismanagement and poor priorities affect every industry (like sinking all your capital into your product, team, or tech, at the expense of probing what customer acquisition really takes and looks like).

This isn't about tech, real estate, or recession-proof luxury products. Fast, cheap, easy money flows into flashy-looking teams with buzzwords, trending industries, and attractive credentials.

If these companies can't show progress or get a profitable CAC, they can't raise more money. They die if they can't raise more money (or slash headcount and find shoestring budget solutions until they solve the real problem).

The kiss of death (and how to avoid it)

If you're running a startup and think raising VC is the answer, pause and evaluate. Do you need the money now?

I'm not saying VC is terrible or has no role. Founders have used it as a Band-Aid for larger, pervasive problems. Venture cash isn't a crutch for recruiting consumers profitably; it's rocket fuel to get you what and who you need.

Pay-to-play isn't a way to throw money at the wall and hope for a return. Pay-to-play works until you run out of money, and if you haven't mastered client acquisition, your cash will diminish quickly.

How can you avoid this bottomless pit? Tips:

• Understand your burn rate

• Keep an eye on your growth or profitability.

• Analyze each and every marketing channel and initiative.

• Make lucrative customer acquisition strategies and satisfied customers your top two priorities. not brand-new products. not stellar hires. avoid the fundraising rollercoaster to save time. If you succeed in these two tasks, investors will approach you with their thirsty offers rather than the other way around, and your cash reserves won't diminish as a result.

Not as much as your grandfather

My family friend always justified expensive, impractical expenditures by saying it was only monopoly money. In business, startups, and especially with money from investors expecting a return, that's not true.

More founders could understand that there isn't always another round if they viewed VC money as their own limited pool. When the well runs dry, you must refill it or save the day.

Venture financing isn't your grandpa's money. A discerning investor has entrusted you with dry powder in the hope that you'll use it wisely, strategically, and thoughtfully. Use it well.

Weekend project: limitless design service. It was fun to see whether I could start a business quickly.

I use no-code apps to save time and resources.

TL;DR I started a business utilizing EditorX for my website, Notion for client project management, and a few favors to finish my portfolio.

First step: research (Day 1)

I got this concept from a Kimp Instagram ad. The Minimalist Hustler Daily newsletter mentioned a similar and cheaper service (Graphically).

I Googled other unlimited design companies. Many provide different costs and services. Some supplied solely graphic design, web development, or copywriting.

Step 2: Brainstorming (Day 1)

I did something simple.

• What benefits and services to provide

• Price to charge

Since it's a one-person performance (for now), I'm focusing on graphic design. I can charge less.

So I don't overwhelm myself and can accommodate budget-conscious clientele.

Step 3: Construction (Day 1 & 2)

This project includes a management tool, a website, and a team procedure.

I built a project management tool and flow first. Once I had the flow and a Notion board, I tested it with design volunteers. They fake-designed while I built the website.

Tool for Project Management

I modified a Notion template. My goal is to keep clients and designers happy.

Team Approach

My sister, my partner, and I kept this business lean. I tweaked the Notion board to make the process smooth. By the end of Sunday, I’d say it’s perfect!

Website

I created the website after they finished the fake design demands. EditorX's drag-and-drop builder attracted me. I didn't need to learn code, and there are templates.

I used a template wireframe.

This project's hardest aspect is developing the site. It's my first time using EditorX and I'm no developer.

People answer all your inquiries in a large community forum.

As a first-time user developing a site in two days, I think I performed OK. Here's the site for feedback.

4th step: testing (Day 2)

Testing is frustrating because it works or doesn't. My testing day was split in two.

• testing the workflow from payment to onboarding to the website

• the demand being tested

It's working so far. If someone gets the trial, they can request design work.

I've gotten a couple of inquiries about demand. I’ll be working with them as a start.

Completion

Finally! I built my side project in one weekend. It's too early to tell if this is successful. I liked that I didn't squander months of resources testing out an idea.

One-hour ebook sales, affiliate relationships, and more.

If you follow me, you may know I started a new ebook in August 2022.

Despite publishing on this platform, my website, and Quora, I'm not a writer.

My writing speed is slow, 2,000 words a day, and I struggle to communicate cohesively.

In April 2022, I wrote a successful guide on How to Write Google-Friendly Blog Posts.

I had no email list or social media presence. I've made $1,600+ selling ebooks.

Evidence:

My first digital offering isn't a book.

It's an actionable guide with my tried-and-true process for writing Google-friendly content.

I'm not bragging.

Established authors like Tim Denning make more from my ebook sales with one newsletter.

This experience taught me writing isn't a privilege.

Writing a book and making money online doesn't require expertise.

Many don't consult experts. They want someone approachable.

Two years passed before I realized my own limits.

I have a brain, two hands, and Internet to spread my message.

I wrote and published a second ebook after the first's success.

On Gumroad, I released my second digital product.

Here's my complete Gumroad evaluation.

Gumroad is a marketplace for content providers to develop and sell sales pages.

Gumroad handles payments and client requests. It's helpful when someone sends a bogus payment receipt requesting an ebook (actual story!).

You'll forget administrative concerns after your first ebook sale.

After my first ebook sale, I did this: I made additional cash!

After every sale, I tell myself, "I built a new semi-passive revenue source."

This thinking shift helps me become less busy while increasing my income and quality of life.

Besides helping others, folks sell evergreen digital things to earn passive money.

It's in my second ebook.

I explain how I built and sold 50+ copies of my SEO writing ebook without being an influencer.

I show how anyone can sell ebooks on Gumroad and automate their sales process.

This is my ebook.

After publicizing the ebook release, I sold three copies within an hour.

Wow, or meh?

I don’t know.

The answer is different for everyone.

These three sales came from a small email list of 40 motivated fans waiting for my ebook release.

I had bigger plans.

I'll market my ebook on Medium, my website, Quora, and email.

I'm testing affiliate partnerships this time.

One of my ebook buyers is now promoting it for 40% commission.

Become my affiliate if you think your readers would like my ebook.

My ebook is a few days old, but I'm interested to see where it goes.

My SEO writing book started without an email list, affiliates, or 4,000 website visitors. I've made four figures.

I'm slowly expanding my communication avenues to have more impact.

Even a small project can open doors you never knew existed.

So began my writing career.

In summary

If you dare, every concept can become a profitable trip.

Before, I couldn't conceive of creating an ebook.

How to Sell eBooks on Gumroad is my second digital product.

Marketing and writing taught me that anything can be sold online.

https://tomconnor.me/wp-content/uploads/2021/08/10x-Engineer-Mental-Models.pdf

I keep returning to the same mental models and tricks after writing and reading about a wide range of topics.

Top 12 mental models

12.

Survival bias - We perceive the surviving population as remarkable, yet they may have gotten there through sheer grit.

Survivorship bias affects us in many situations. Our retirement fund; the unicorn business; the winning team. We often study and imitate the last one standing. This can lead to genuine insights and performance improvements, but it can also lead us astray because the leader may just be lucky.

11.

The Helsinki Bus Theory - How to persevere Buss up!

Always display new work, and always be compared to others. Why? Easy. Keep riding. Stay on the fucking bus.

10.

Until it sticks… Turning up every day… — Artists teach engineers plenty. Quality work over a career comes from showing up every day and starting.

9.

WRAP decision making process (Heath Brothers)

Decision-making WRAP Model:

W — Widen your Options

R — Reality test your assumptions

A — Attain Distance

P — Prepare to be wrong or Right

8.

Systems for knowledge worker excellence - Todd Henry and Cal Newport write about techniques knowledge workers can employ to build a creative rhythm and do better work.

Todd Henry's FRESH framework:

1. Focus: Keep the start in mind as you wrap up.

2. Relationships: close a loop that's open.

3. Pruning is an energy.

4. Set aside time to be inspired by stimuli.

5. Hours: Spend time thinking.

7.

Black Box Thinking…..

BBT is learning from mistakes. Science has transformed the world because it constantly updates its theories in light of failures. Complexity guarantees failure. Do we learn or self-justify?

6.

The OODA Loop - Competitive advantage

O: Observe: collect the data. Figure out exactly where you are, what’s happening.

O: Orient: analyze/synthesize the data to form an accurate picture.

D: Decide: select an action from possible options

A: Action: execute the action, and return to step (1)

Boyd's approach indicates that speed and agility are about information processing, not physical reactions. They form feedback loops. More OODA loops improve speed.

5.

Know your Domain 

Leaders who try to impose order in a complex situation fail; those who set the stage, step back, and allow patterns to develop win.

https://vimeo.com/640941172?embedded=true&source=vimeo_logo&owner=11999906

4.

The Three Critical Gaps

• Information Gap - The discrepancy between what we know and what we would like to know

• Gap in Alignment - What individuals actually do as opposed to what we wish them to do

• Effects Gap - the discrepancy between our expectations and the results of our actions

3.

Theory of Constraints — The Goal  - To maximize system production, maximize bottleneck throughput.

• Goldratt creates a five-step procedure:

1. Determine the restriction

2. Improve the restriction.

3. Everything else should be based on the limitation.

4. Increase the restriction

5. Go back to step 1 Avoid letting inertia become a limitation.

Any non-constraint improvement is an illusion.

2.

Serendipity and the Adjacent Possible - Why do several amazing ideas emerge at once? How can you foster serendipity in your work?

You need specialized abilities to reach to the edge of possibilities, where you can pursue exciting tasks that will change the world. Few people do it since it takes a lot of hard work. You'll stand out if you do.

Most people simply lack the comfort with discomfort required to tackle really hard things. At some point, in other words, there’s no way getting around the necessity to clear your calendar, shut down your phone, and spend several hard days trying to make sense of the damn proof.

1.

Boundaries of failure - Rasmussen's accident model.

Rasmussen modeled this. It has economic, workload, and performance boundaries.

The economic boundary is a company's profit zone. If the lights are on, you're within the economic boundaries, but there's pressure to cut costs and do more.

Performance limit reflects system capacity. Taking shortcuts is a human desire to minimize work. This is often necessary to survive because there's always more labor.

Both push operating points toward acceptable performance. Personal or process safety, or equipment performance.

If you exceed acceptable performance, you'll push back, typically forcefully.

Reddit's NFT market is alive and well.

NFT owners outnumber OpenSea on Reddit.

Reddit NFTs flip in OpenSea in days:

Fast-selling.

NFT sales will make Reddit's current communities more engaged.

I don't think NFTs will affect existing groups, but they will build hype for people to acquire them.

The first season of Collectibles is unique, but many missed the first season.

Second-season NFTs are less likely to be sold for a higher price than first-season ones.

If you use Reddit, it's fun to own NFTs.