Wishing for Lasting Companies, Not Penny Stocks or Goodwill Write-Downs

Get me a NASCAR-style company-logoed cremation urn (notice to the executor of my will, theres gonna be a lot of weird requests). I believe in working on projects that would be on your tombstone. As the Homebrew logo is tattooed on my shoulder, expanding the portfolio to my posthumous commemoration is easy. But this isn't an IRR victory lap; it's a hope that the firms we worked for would last beyond my lifetime.

Venture investors too often take credit or distance themselves from startups based on circumstances. Successful companies tell stories of crucial introductions, strategy conversations, and other value. Defeats Even whether our term involves Board service or systematic ethical violations, I'm just a little investment, so there's not much I can do. Since I'm guilty, I'm tossing stones from within the glass home (although we try to own our decisions through the lifecycle).

Post-exit company trajectories are usually unconfounded. Off the cap table, no longer a shareholder (or a diminishing one as you sell off/distribute), eventually leaving the Board. You can cheer for the squad or forget about it, but you've freed the corporation and it's back to portfolio work.

As I look at the downward track of most SPACs and other tarnished IPOs from the last few years, I wonder how I would feel if those were my legacy. Is my job done? Yes. When investing in a business, the odds are against it surviving, let alone thriving and being able to find sunlight. SPAC sponsors, institutional buyers, retail investments. Free trade in an open market is their right. Risking and losing capital is the system working! But

We were lead or co-lead investors in our first three funds, but as additional VCs joined the company, we were pushed down the cap table. Voting your shares rarely matters; supporting the firm when they need it does. Being valuable, consistent, and helping the company improve builds trust with the founders.

I hope every startup we sponsor becomes a successful public company before, during, and after we benefit. My perspective of American capitalism. Well, a stock ticker has a lot of garbage, and I support all types of regulation simplification (in addition to being a person investor in the Long-Term Stock Exchange). Yet being owned by a large group of investors and making actual gains for them is great. Likewise does seeing someone you met when they were just starting out become a public company CEO without losing their voice, leadership, or beliefs.

I'm just thinking about what we can do from the start to realize value from our investments and build companies with bright futures. Maybe seed venture financing shouldn't impact those outcomes, but I'm not comfortable giving up that obligation.

Product game mindsets? How do these vary from Project mindset?

1950s spawned the Iron Triangle. Project people everywhere know and live by it. In stakeholder meetings, it is used to stretch the timeframe, request additional money, or reduce scope.

Quality was added to this triangle as things matured.

Quality was intended to be transformative, but none of these principles addressed why we conduct projects.

Value and benefits are key.

Product value is quantified by ROI, revenue, profit, savings, or other metrics. For me, every project or product delivery is about value.

Most project managers, especially those schooled 5-10 years or more ago (thousands working in huge corporations worldwide), understand the world in terms of the iron triangle. What does that imply? They worry about:

a) enough time to get the thing done.

b) have enough resources (budget) to get the thing done.

c) have enough scope to fit within (a) and (b) >> note, they never have too little scope, not that I have ever seen! although, theoretically, this could happen.

Boom—iron triangle.

To make the triangle function, project managers will utilize formal governance (Steering) to move those things. Increase money, scope, or both if time is short. Lacking funds? Increase time, scope, or both.

In current product development, shifting each item considerably may not yield value/benefit.

Even terrible. This approach will fail because it deprioritizes Value/Benefit by focusing the major stakeholders (Steering participants) and delivery team(s) on Time, Scope, and Budget restrictions.

Pre-agile, this problem was terrible. IT projects failed wildly. History is here.

Value, or benefit, is central to the product method. Product managers spend most of their time planning value-delivery paths.

Product people consider risk, schedules, scope, and budget, but value comes first. Let me illustrate.

Imagine managing internal products in an enterprise. Your core customer team needs a rapid text record of a chat to fix a problem. The consumer wants a feature/features added to a product you're producing because they think it's the greatest spot.

Project-minded, I may say;

Ok, I have budget as this is an existing project, due to run for a year. This is a new requirement to add to the features we’re already building. I think I can keep the deadline, and include this scope, as it sounds related to the feature set we’re building to give the desired result”.

This attitude repeats Scope, Time, and Budget.

Since it meets those standards, a project manager will likely approve it. If they have a backlog, they may add it and start specking it out assuming it will be built.

Instead, think like a product;

What problem does this feature idea solve? Is that problem relevant to the product I am building? Can that problem be solved quicker/better via another route ? Is it the most valuable problem to solve now? Is the problem space aligned to our current or future strategy? or do I need to alter/update the strategy?

A product mindset allows you to focus on timing, resource/cost, feasibility, feature detail, and so on after answering the aforementioned questions.

The above oversimplifies because

Leadership in discovery

Project managers are facilitators of ideas. This is as far as they normally go in the ‘idea’ space.

Business Requirements collection in classic project delivery requires extensive upfront documentation.

Agile project delivery analyzes requirements iteratively.

However, the project manager is a facilitator/planner first and foremost, therefore topic knowledge is not expected.

I mean business domain, not technical domain (to confuse matters, it is true that in some instances, it can be both technical and business domains that are important for a single individual to master).

Product managers are domain experts. They will become one if they are training/new.

They lead discovery.

Product Manager-led discovery is much more than requirements gathering.

Requirements gathering involves a Business Analyst interviewing people and documenting their requests.

The project manager calculates what fits and what doesn't using their Iron Triangle (presumably in their head) and reports back to Steering.

If this requirements-gathering exercise failed to identify requirements, what would a project manager do? or bewildered by project requirements and scope?

They would tell Steering they need a Business SME or Business Lead assigning or more of their time.

Product discovery requires the Product Manager's subject knowledge and a new mindset.

How should a Product Manager handle confusing requirements?

Product Managers handle these challenges with their talents and tools. They use their own knowledge to fill in ambiguity, but they have the discipline to validate those assumptions.

To define the problem, they may perform qualitative or quantitative primary research.

They might discuss with UX and Engineering on a whiteboard and test assumptions or hypotheses.

Do Product Managers escalate confusing requirements to Steering/Senior leaders? They would fix that themselves.

Product managers raise unclear strategy and outcomes to senior stakeholders. Open talks, soft skills, and data help them do this. They rarely raise requirements since they have their own means of handling them without top stakeholder participation.

Discovery is greenfield, exploratory, research-based, and needs higher-order stakeholder management, user research, and UX expertise.

Product Managers also aid discovery. They lead discovery. They will not leave customer/user engagement to a Business Analyst. Administratively, a business analyst could aid. In fact, many product organizations discourage business analysts (rely on PM, UX, and engineer involvement with end-users instead).

The Product Manager must drive user interaction, research, ideation, and problem analysis, therefore a Product professional must be skilled and confident.

Creating vs. receiving and having an entrepreneurial attitude

Product novices and project managers focus on details rather than the big picture. Project managers prefer spreadsheets to strategy whiteboards and vision statements.

These folks ask their manager or senior stakeholders, "What should we do?"

They then elaborate (in Jira, in XLS, in Confluence or whatever).

They want that plan populated fast because it reduces uncertainty about what's going on and who's supposed to do what.

Skilled Product Managers don't only ask folks Should we?

They're suggesting this, or worse, Senior stakeholders, here are some options. After asking and researching, they determine what value this product adds, what problems it solves, and what behavior it changes.

Therefore, to move into Product, you need to broaden your view and have courage in your ability to discover ideas, find insightful pieces of information, and collate them to form a valuable plan of action. You are constantly defining RoI and building Business Cases, so much so that you no longer create documents called Business Cases, it is simply ingrained in your work through metrics, intelligence, and insights.

Product Management is not a free lunch.

Plateless.

Plates and food must be prepared.

In conclusion, Product Managers must make at least three mentality shifts:

1. You put value first in all things. Time, money, and scope are not as important as knowing what is valuable.

2. You have faith in the field and have the ability to direct the search. YYou facilitate, but you don’t just facilitate. You wouldn't want to limit your domain expertise in that manner.

3. You develop concepts, strategies, and vision. You are not a waiter or an inbox where other people can post suggestions; you don't merely ask folks for opinion and record it. However, you excel at giving things that aren't clearly spoken or written down physical form.

How much do startup founders make after an IPO? We looked at 2018's major tech IPOs. Paydays aren't what founders took home at the IPO (shares are normally locked up for 6 months), but what they were worth at the IPO price on the day the firm went public. It's not cash, but it's nice. Here's the data.

Several points are noteworthy.

Huge payoffs. Median and average pay were $399m and $918m. Average and median homeownership were 9% and 12%.

Coinbase, Uber, UI Path. Uber, Zoom, Spotify, UI Path, and Coinbase founders raised billions. Zoom's founder owned 19% and Spotify's 28% and 13%. Brian Armstrong controlled 20% of Coinbase at IPO and was worth $15bn. Preserving as much equity as possible by staying cash-efficient or raising at high valuations also helps.

The smallest was Ping. Ping's compensation was the smallest. Andre Duand owned 2% but was worth $20m at IPO. That's less than some billion-dollar paydays, but still good.

IPOs can be lucrative, as you can see. Preserving equity could be the difference between a $20mm and $15bln payday (Coinbase).

Three Arrows Capital's Google search volume rose over 5,000%.

Three Arrows Capital, a Singapore-based cryptocurrency hedge fund, filed for Chapter 15 bankruptcy last Friday to protect its U.S. assets from creditors.

• Three Arrows filed for bankruptcy on July 1 in New York.

• Three Arrows was ordered liquidated by a British Virgin Islands court last week after defaulting on a $670 million loan from Voyager Digital. Three days later, the Singaporean government reprimanded Three Arrows for spreading misleading information and exceeding asset limits.

• Three Arrows' troubles began with Terra's collapse in May, after it bought US$200 million worth of Terra's LUNA tokens in February, co-founder Kyle Davies told the Wall Street Journal. Three Arrows has failed to meet multiple margin calls since then, including from BlockFi and Genesis.

• Three Arrows Capital, founded by Kyle Davies and Su Zhu in 2012, manages $10 billion in crypto assets.

• Bitcoin's price fell from US$20,600 to below US$19,200 after Three Arrows' bankruptcy petition. According to CoinMarketCap, BTC is now above US$20,000.

What does it mean?

Every action causes an equal and opposite reaction, per Newton's third law. Newtonian physics won't comfort Three Arrows investors, but future investors will thank them for their overconfidence.

Regulators are taking notice of crypto's meteoric rise and subsequent fall. Historically, authorities labeled the industry "high risk" to warn traditional investors against entering it. That attitude is changing. Regulators are moving quickly to regulate crypto to protect investors and prevent broader asset market busts.

The EU has reached a landmark deal that will regulate crypto asset sales and crypto markets across the 27-member bloc. The U.S. is close behind with a similar ruling, and smaller markets are also looking to improve safeguards.

For many, regulation is the only way to ensure the crypto industry survives the current winter.

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.

Restructuring and layoffs cause career reevaluation. Your career can benefit.

Once you become institutionalized, the corporate ladder is all you know.

You're bubbled. Extremists term it the corporate Matrix. I'm not so severe because the business world brainwashed me, too.

This boosted my corporate career.

Until I hit bottom.

15 months later, I view my corporate life differently. You may wish to advance professionally. Read this before you do.

Your happiness in the workplace may be deceptive.

I've been fortunate to spend time with corporate aces.

Working for 2.5 years in banking social media gave me some of these experiences. Earlier in my career, I recorded interviews with business leaders.

These people have titles like Chief General Manager and Head Of. New titles brought life-changing salaries.

They seemed happy.

I’d pass them in the hallway and they’d smile or shake my hand. I dreamt of having their life.

The ominous pattern

Unfiltered talks with some of them revealed a different world.

They acted well. They were skilled at smiling and saying the correct things. All had the same dark pattern, though.

Something felt off.

I found my conversations with them were generally for their benefit. They hoped my online antics as a writer/coach would shed light on their dilemma.

They'd tell me they wanted more. When you're one position away from CEO, it's hard not to wonder if this next move will matter.

What really displeased corporate ladder chasers

Before ascending further, consider these.

Zero autonomy

As you rise in a company, your days get busier.

Many people and initiatives need supervision. Everyone expects you to know business details. Weak when you don't. A poor leader is fired during the next restructuring and left to pursue their corporate ambition.

Full calendars leave no time for reflection. You can't have a coffee with a friend or waste a day.

You’re always on call. It’s a roll call kinda life.

Unable to express oneself freely

My 8 years of LinkedIn writing helped me meet these leaders.

I didn't think they'd care. Mistake.

Corporate leaders envied me because they wanted to talk freely again without corporate comms or a PR firm directing them what to say.

They couldn't share their flaws or inspiring experiences.

They wanted to.

Every day they were muzzled eroded by their business dream.

Limited family time

Top leaders had families.

They've climbed the corporate ladder. Nothing excellent happens overnight.

Corporate dreamers rarely saw their families.

Late meetings, customer functions, expos, training, leadership days, team days, town halls, and product demos regularly occurred after work.

Or they had to travel interstate or internationally for work events. They used bags and motel showers.

Initially, they said business class flights and hotels were nice. They'd get bored. 5-star hotels become monotonous.

No hotel beats home.

One leader said he hadn't seen his daughter much. They used to Facetime, but now that he's been gone so long, she rarely wants to talk to him.

So they iPad-parented.

You're miserable without your family.

Held captive by other job titles

Going up the business ladder seems like a battle.

Leaders compete for business gains and corporate advancement.

I saw shocking filthy tricks. Leaders would lie to seem nice.

Captives included top officials.

A different section every week. If they ran technology, the Head of Sales would argue their CRM cost millions. Or an Operations chief would battle a product team over support requests.

After one conflict, another began.

Corporate echelons are antagonistic. Huge pay and bonuses guarantee bad behavior.

Overly centered on revenue

As you rise, revenue becomes more prevalent. Most days, you'd believe revenue was everything. Here’s the problem…

Numbers drain us.

Unless you're a closet math nerd, contemplating and talking about numbers drains your creativity.

Revenue will never substitute impact.

Incapable of taking risks

Corporate success requires taking fewer risks.

Risks can cause dismissal. Risks can interrupt business. Keep things moving so you may keep getting paid your enormous salary and bonus.

Restructuring or layoffs are inevitable. All corporate climbers experience it.

On this fateful day, a small few realize the game they’ve been trapped in and escape. Most return to play for a new company, but it takes time.

Addiction keeps them trapped. You know nothing else. The rest is strange.

You start to think “I’m getting old” or “it’s nearly retirement.” So you settle yet again for the trappings of the corporate ladder game to nowhere.

Should you climb the corporate ladder?

Let me end on a surprising note.

Young people should ascend the corporate ladder. It teaches you business skills and helps support your side gig and (potential) online business.

Don't get trapped, shackled, or muzzled.

Your ideas and creativity become stifled after too much gaming play.

Corporate success won't bring happiness.

Find fulfilling employment that matters. That's it.