Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!

It’s Zuora’s, and it’s brilliant. Here’s why.

My friend Tim got a sales position at a Series-C software company that garnered $60 million from A-list investors. He's one of the best salespeople I know, yet he emailed me after starting to struggle.

Tim has a few modest clients. “Big companies ignore my pitch”. Tim said.

I love helping teams write the strategic story that drives sales, marketing, and fundraising. Tim and I had lunch at Amber India on Market Street to evaluate his deck.

After a feast, I asked Tim when prospects tune out.

He said, “several slides in”.

Intent on maximizing dining ROI, Tim went back to the buffet for seconds. When he returned, I pulled out my laptop and launched into a Powerpoint presentation.

“What’s this?” Tim asked.

“This,” I said, “is the greatest sales deck I have ever seen.”

Five Essentials of a Great Sales Narrative

I showed Tim a sales slide from IPO-bound Zuora, which sells a SaaS platform for subscription billing. Zuora supports recurring payments (e.g. enterprise software).

Ex-Zuora salesman gave me the deck, saying it helped him close his largest business. (I don't know anyone who works at Zuora.) After reading this, a few Zuora employees contacted me.)

Tim abandoned his naan in a pool of goat curry and took notes while we discussed the Zuora deck.

We remarked how well the deck led prospects through five elements:

(The ex-Zuora salesperson begged me not to release the Zuora deck publicly.) All of the images below originate from Zuora's website and SlideShare channel.)

#1. Name a Significant Change in the World

Don't start a sales presentation with mentioning your product, headquarters, investors, clients, or yourself.

Name the world shift that raises enormous stakes and urgency for your prospect.

Every Zuora sales deck begins with this slide:

Zuora coined the term subscription economy to describe a new market where purchasers prefer regular service payments over outright purchases. Zuora then shows a slide with the change's history.

Most pitch recommendation advises starting with the problem. When you claim a problem, you put prospects on the defensive. They may be unaware of or uncomfortable admitting the situation.

When you highlight a global trend, prospects open up about how it affects them, worries them, and where they see opportunity. You capture their interest. Robert McKee says:

…what attracts human attention is change. …if the temperature around you changes, if the phone rings — that gets your attention. The way in which a story begins is a starting event that creates a moment of change.

#2. Show There’ll Be Winners and Losers

Loss aversion affects all prospects. They avoid a loss by sticking with the status quo rather than risking a gain by changing.

To fight loss aversion, show how the change will create winners and losers. You must show both

1. that if the prospect can adjust to the modification you mentioned, the outcome will probably be quite favorable; and

2. That failing to do so is likely to have an unacceptable negative impact on the prospect's future

Zuora shows a mass extinction among Fortune 500 firms.

…and then showing how the “winners” have shifted from product ownership to subscription services. Those include upstarts…

…as well as rejuvenated incumbents:

To illustrate, Zuora asks:

Winners utilize Zuora's subscription service models.

#3. Tease the Promised Land

It's tempting to get into product or service details now. Resist that urge.

Prospects won't understand why product/service details are crucial if you introduce them too soon, therefore they'll tune out.

Instead, providing a teaser image of the happily-ever-after your product/service will assist the prospect reach.

Your Promised Land should be appealing and hard to achieve without support. Otherwise, why does your company exist?

Zuora shows this Promised Land slide after explaining that the subscription economy will have winners and losers.

Not your product or service, but a new future state.

(I asked my friend Tim to describe his Promised Land, and he answered, "You’ll have the most innovative platform for ____." Nope: the Promised Land isn't possessing your technology, but living with it.)

Your Promised Land helps prospects market your solution to coworkers after your sales meeting. Your coworkers will wonder what you do without you. Your prospects are more likely to provide a persuasive answer with a captivating Promised Land.

#4. Present Features as “Mystic Gifts” for Overcoming Difficulties on the Road to the Promised Land

Successful sales decks follow the same format as epic films and fairy tales. Obi Wan gives Luke a lightsaber to help him destroy the Empire. You're Gandalf, helping Frodo destroy the ring. Your prospect is Cinderella, and you're her fairy godmother.

Position your product or service's skills as mystical gifts to aid your main character (prospect) achieve the Promised Land.

Zuora's client record slide is shown above. Without context, even the most technical prospect would be bored.

Positioned in the context of shifting from an “old” to a “new world”, it's the foundation for a compelling conversation with prospects—technical and otherwise—about why traditional solutions can't reach the Promised Land.

#5. Show Proof That You Can Make the Story True.

In this sense, you're promising possibilities that if they follow you, they'll reach the Promised Land.

The journey to the Promised Land is by definition rocky, so prospects are right to be cautious. The final part of the pitch is proof that you can make the story come true.

The most convincing proof is a success story about how you assisted someone comparable to the prospect. Zuora's sales people use a deck of customer success stories, but this one gets the essence.

I particularly appreciate this one from an NCR exec (a Zuora customer), which relates more strongly to Zuora's Promised Land:

Not enough successful customers? Product demos are the next best evidence, but features should always be presented in the context of helping a prospect achieve the Promised Land.

The best sales narrative is one that is told by everyone.

Success rarely comes from a fantastic deck alone. To be effective, salespeople need an organization-wide story about change, Promised Land, and Magic Gifts.

Zuora exemplifies this. If you hear a Zuora executive, including CEO Tien Tzuo, talk, you'll likely hear about the subscription economy and its winners and losers. This is the theme of the company's marketing communications, campaigns, and vision statement.

According to the ex-Zuora salesperson, company-wide story alignment made him successful.

The Zuora marketing folks ran campaigns and branding around this shift to the subscription economy, and [CEO] Tien [Tzuo] talked it up all the time. All of that was like air cover for my in-person sales ground attack. By the time I arrived, prospects were already convinced they had to act. It was the closest thing I’ve ever experienced to sales nirvana.

The largest deal ever

Tim contacted me three weeks after our lunch to tell me that prospects at large organizations were responding well to his new deck, which we modeled on Zuora's framework. First, prospects revealed their obstacles more quickly. The new pitch engages CFOs and other top gatekeepers better, he said.

A week later, Tim emailed that he'd signed his company's biggest agreement.

Next week, we’re headed back to Amber India to celebrate.

People are slowly recognizing entrepreneurship's downside.

Growing up, entrepreneurship wasn't common. High school class of 2012 had no entrepreneurs.

Businesses were different.

They had staff and a lengthy history of achievement.

I never wanted a business. It felt unattainable. My friends didn't care.

Weird.

People desired degrees to attain good jobs at big companies.

When graduated high school:

• 9 out of 10 people attend college

• Earn minimum wage (7%) working in a restaurant or retail establishment

• Or join the military (3%)

Later, entrepreneurship became a thing.

2014-ish

I was in the military and most of my high school friends were in college, so I didn't hear anything.

Entrepreneurship soared in 2015, according to Google Trends.

Then more individuals were interested. Entrepreneurship went from unusual to cool.

In 2015, it was easier than ever to build a website, run Facebook advertisements, and achieve organic social media reach.

There were several online business tools.

You didn't need to spend years or money figuring it out. Most entry barriers were gone.

Everyone wanted a side gig to escape the 95.

Small company applications have increased during the previous 10 years.

2011-2014 trend continues.

2015 adds 150,000 applications. 2016 adds 200,000. Plus 300,000 in 2017.

The graph makes it look little, but that's a considerable annual spike with no indications of stopping.

By 2021, new business apps had doubled.

Entrepreneurship will return to its early 2010s level.

I think we'll go backward in 5 years.

Entrepreneurship is half as popular as it was in 2015.

In the late 2020s and 30s, entrepreneurship will again be obscure.

Entrepreneurship's decade-long splendor is fading. People will cease escaping 9-5 and launch fewer companies.

That’s not a bad thing.

I think people have a rose-colored vision of entrepreneurship. It's fashionable. People feel that they're missing out if they're not entrepreneurial.

Reality is showing up.

People say on social media, "I knew starting a business would be hard, but not this hard."

More negative posts on entrepreneurship:

Luke adds:

Is being an entrepreneur ‘healthy’? I don’t really think so. Many like Gary V, are not role models for a well-balanced life. Despite what feel-good LinkedIn tells you the odds are against you as an entrepreneur. You have to work your face off. It’s a tough but rewarding lifestyle. So maybe let’s stop glorifying it because it takes a lot of (bleepin) work to survive a pandemic, mental health battles, and a competitive market.

Entrepreneurship is no longer a pipe dream.

It’s hard.

I went full-time in March 2020. I was done by April 2021. I had a good-paying job with perks.

When that fell through (on my start date), I had to continue my entrepreneurial path. I needed money by May 1 to pay rent.

Entrepreneurship isn't as great as many think.

Entrepreneurship is a serious business.

If you have a 9-5, the grass isn't greener here. Most people aren't telling the whole story when they post on social media or quote successful entrepreneurs.

People prefer to communicate their victories than their defeats.

Is this a bad thing?

I don’t think so.

Over the previous decade, entrepreneurship went from impossible to the finest thing ever.

It peaked in 2020-21 and is returning to reality.

Startups aren't for everyone.

If you like your job, don't quit.

Entrepreneurship won't amaze people if you quit your job.

It's irrelevant.

You're doomed.

And you'll probably make less money.

If you hate your job, quit. Change jobs and bosses. Changing jobs could net you a greater pay or better perks.

When you go solo, your paycheck and perks vanish. Did I mention you'll fail, sleep less, and stress more?

Nobody will stop you from pursuing entrepreneurship. You'll face several challenges.

Possibly.

Entrepreneurship may be romanticized for years.

Based on what I see from entrepreneurs on social media and trends, entrepreneurship is challenging and few will succeed.

Elon Musk, Matt Taibbi, the 'Twitter Files,' and Hunter Biden's laptop: what gives?

Explaining Twitter Files

Matt Taibbi released "The Twitter Files," a batch of emails sent by Twitter executives discussing the company's decision to stop an October 2020 New York Post story online.

What's on Twitter? New York Post and Fox News call them "bombshell" documents. Or, as a Post columnist admitted, are they "not the smoking gun"? Onward!

What started this?

The New York Post published an exclusive, potentially explosive story in October 2020: Biden's Secret Emails: Ukrainian executive thanks Hunter Biden for'meeting' veep dad. The story purported to report the contents of a laptop brought to the tabloid by a Delaware computer repair shop owner who said it belonged to President Biden's second son, Hunter Biden. Emails and files on the laptop allegedly showed how Hunter peddled influence with Ukranian businessmen and included a "raunchy 12-minute video" of Hunter smoking crack and having sex.

Twitter banned links to the Post story after it was published, calling it "hacked material." The Post's Twitter account was suspended for multiple days.

Why? Yoel Roth, Twitter's former head of trust and safety, said the company couldn't verify the story, implying they didn't trust the Post.

Twitter's stated purpose rarely includes verifying news stories. This seemed like intentional political interference. This story was hard to verify because the people who claimed to have found the laptop wouldn't give it to other newspapers. (Much of the story, including Hunter's business dealings in Ukraine and China, was later confirmed.)

Roth: "It looked like a hack and leak."

So what are the “Twitter Files?”

Twitter's decision to bury the story became a political scandal, and new CEO Elon Musk promised an explanation. The Twitter Files, named after Facebook leaks.

Musk promised exclusive details of "what really happened" with Hunter Biden late Friday afternoon. The tweet was punctuated with a popcorn emoji.

Explaining Twitter Files

Three hours later, journalist Matt Taibbi tweeted more than three dozen tweets based on internal Twitter documents that revealed "a Frankensteinian tale of a human-built mechanism grown out of its designer's control."

Musk sees this release as a way to shape Twitter's public perception and internal culture in his image. We don't know if the CEO gave Taibbi the documents. Musk hyped the document dump before and during publication, but Taibbi cited "internal sources."

Taibbi shares email screenshots showing Twitter execs discussing the Post story and blocking its distribution. Taibbi says the emails show Twitter's "extraordinary steps" to bury the story.

Twitter communications chief Brandon Borrman has the most damning quote in the Files. Can we say this is policy? The story seemed unbelievable. It seemed like a hack... or not? Could Twitter, which ex-CEO Dick Costolo called "the free speech wing of the free speech party," censor a news story?

Many on the right say the Twitter Files prove the company acted at the behest of Democrats. Both parties had these tools, writes Taibbi. In 2020, both the Trump White House and Biden campaign made requests. He says the system for reporting tweets for deletion is unbalanced because Twitter employees' political donations favor Democrats. Perhaps. These donations may have helped Democrats connect with Twitter staff, but it's also possible they didn't. No emails in Taibbi's cache show these alleged illicit relations or any actions Twitter employees took as a result.

Even Musk's supporters were surprised by the drop. Miranda Devine of the New York Post told Tucker Carlson the documents weren't "the smoking gun we'd hoped for." Sebastian Gorka said on Truth Social, "So far, I'm deeply underwhelmed." DC Democrats collude with Palo Alto Democrats. Whoop!” The Washington Free Beacon's Joe Simonson said the Twitter files are "underwhelming." Twitter was staffed by Democrats who did their bidding. (Why?)

If "The Twitter Files" matter, why?

These emails led Twitter to suppress the Hunter Biden laptop story has real news value. It's rare for a large and valuable company like Twitter to address wrongdoing so thoroughly. Emails resemble FOIA documents. They describe internal drama at a company with government-level power. Katie Notopoulos tweeted, "Any news outlet would've loved this scoop!" It's not a'scandal' as teased."

Twitter's new owner calls it "the de facto public town square," implying public accountability. Like a government agency. Though it's exciting to receive once-hidden documents in response to a FOIA, they may be boring and tell you nothing new. Like Twitter files. We learned how Twitter blocked the Post's story, but not why. Before these documents were released, we knew Twitter had suppressed the story and who was involved.

These people were disciplined and left Twitter. Musk fired Vijaya Gadde, the former CLO who reportedly played a "key role" in the decision. Roth quit over Musk's "dictatorship." Musk arrived after Borrman left. Jack Dorsey, then-CEO, has left. Did those who digitally quarantined the Post's story favor Joe Biden and the Democrats? Republican Party opposition and Trump hatred? New York Post distaste? According to our documents, no. Was there political and press interference? True. We knew.

Taibbi interviewed anonymous ex-Twitter employees about the decision; all expressed shock and outrage. One source said, "Everyone knew this was fucked." Since Taibbi doesn't quote that expletive, we can assume the leaked emails contained few or no sensational quotes. These executives said little to support nefarious claims.

Outlets more invested in the Hunter Biden story than Gizmodo seem vexed by the release and muted headlines. The New York Post, which has never shied away from a blaring headline in its 221-year history, owns the story of Hunter Biden's laptop. Two Friday-night Post alerts about Musk's actions were restrained. Elon Musk will drop Twitter files on NY Post-Hunter Biden laptop censorship today. Elon Musk's Twitter dropped Post censorship details from Biden's laptop. Fox News' Apple News push alert read, "Elon Musk drops Twitter censorship documents."

Bombshell, bombshell, bombshell… what, exactly, is the bombshell? Maybe we've heard this story too much and are missing the big picture. Maybe these documents detail a well-documented decision.

The Post explains why on its website. "Hunter Biden laptop bombshell: Twitter invented reason to censor Post's reporting," its headline says.

Twitter's ad hoc decision to moderate a tabloid's content is not surprising. The social network had done this for years as it battled toxic users—violent white nationalists, virulent transphobes, harassers and bullies of all political stripes, etc. No matter how much Musk crows, the company never had content moderation under control. Buzzfeed's 2016 investigation showed how Twitter has struggled with abusive posters since 2006. Jack Dorsey and his executives improvised, like Musk.

Did the US government interfere with the ex-social VP's media company? That's shocking, a bombshell. Musk said Friday, "Twitter suppressing free speech by itself is not a 1st amendment violation, but acting under government orders with no judicial review is." Indeed! Taibbi believed this. August 2022: "The laptop is secondary." Zeynep Tufecki, a Columbia professor and New York Times columnist, says the FBI is cutting true story distribution. Taibbi retracted the claim Friday night: "I've seen no evidence of government involvement in the laptop story."

What’s the bottom line?

I'm still not sure what's at stake in the Hunter Biden scandal after dozens of New York Post articles, hundreds of hours of Fox News airtime, and thousands of tweets. Briefly: Joe Biden's son left his laptop with a questionable repairman. FBI confiscated it? The repairman made a copy and gave it to Rudy Giuliani's lawyer. The Post got it from Steve Bannon. On that laptop were videos of Hunter Biden smoking crack, cavorting with prostitutes, and emails about introducing his father to a Ukrainian businessman for $50,000 a month. Joe Biden urged Ukraine to fire a prosecutor investigating the company. What? The story seems to be about Biden family business dealings, right?

The discussion has moved past that point anyway. Now, the story is the censorship of it. Adrienne Rich wrote in "Diving Into the Wreck" that she came for "the wreck and not the story of the wreck" No matter how far we go, Hunter Biden's laptop is done. Now, the crash's story matters.

I'm dizzy. Katherine Miller of BuzzFeed wrote, "I know who I believe, and you probably do, too. To believe one is to disbelieve the other, which implicates us in the decision; we're stuck." I'm stuck. Hunter Biden's laptop is a political fabrication. You choose. I've decided.

This could change. Twitter Files drama continues. Taibbi said, "Much more to come." I'm dizzy.

How to reframe irritation and go forward

“… before you can figure out where you are going, you need to know where you are, and once you know and accept where you are, you can design your way to where you want to be.” — Bill Burnett and Dave Evans

“You’ve been here before. But there are some new ingredients this time. What can tell yourself that will make you understand that now isn’t just like last year? That there’s something new in this August.”

My coach paused. I sighed, inhaled deeply, and considered her question.

What could I say? I simply needed a plan from her so everything would fall into place and I could be the happy, successful person I want to be.

Time passed. My mind was exhausted from running all morning, all summer, or the last five years, searching for what to do next and how to get there.

Calmer, I remembered that my coach's inquiry had benefited me throughout the summer. The month before our call, I read Designing Your Work Life — How to Thrive and Change and Find Happiness at Work from Standford University’s Bill Burnett and Dave Evans.

A passage in their book felt like a lifeline: “We have something important to say to you: Wherever you are in your work life, whatever job you are doing, it’s good enough. For now. Not forever. For now.”

As I remembered this book on the coaching call, I wondered if I could embrace where I am in August and say my job life is good enough for now. Only temporarily.

I've done that since. I'm getting unstuck.

Here's how you can take the first step in any area where you feel stuck.

How to acquire the perspective of "Good enough for now" for yourself

We’ve all heard the advice to just make the best of a bad situation. That´s not bad advice, but if you only make the best of a bad situation, you are still in a bad situation. It doesn’t get to the root of the problem or offer an opportunity to change the situation. You’re more cheerfully navigating lousiness, which is an improvement, but not much of one and rather hard to sustain over time.” — Bill Burnett and Dave Evans

Reframing Burnett at Evans says good enough for now is the key to being happier at work. Because, as they write, a designer always has options.

Choosing to believe things are good enough for now is liberating. It helps us feel less victimized and less judged. Accepting our situation helps us become unstuck.

Let's break down the process, which designers call constructing your way ahead, into steps you can take today.

Writing helps get started. First, write down your challenge and why it's essential to you. If pen and paper help, try this strategy:

• Make the decision to accept the circumstance as it is. Designers always begin by acknowledging the truth of the situation. You now refrain from passing judgment. Instead, you simply describe the situation as accurately as you can. This frees us from negative thought patterns that prevent us from seeing the big picture and instead keep us in a tunnel of negativity.

• Look for a reframing right now. Begin with good enough for the moment. Take note of how your body feels as a result. Tell yourself repeatedly that whatever is occurring is sufficient for the time being. Not always, but just now. If you want to, you can even put it in writing and repeatedly breathe it in, almost like a mantra.

• You can select a reframe that is more relevant to your situation once you've decided that you're good enough for now and have allowed yourself to believe it. Try to find another perspective that is possible, for instance, if you feel unappreciated at work and your perspective of I need to use and be recognized for all my new skills in my job is making you sad and making you want to resign. For instance, I can learn from others at work and occasionally put my new abilities to use.

• After that, leave your mind and act in accordance with your new perspective. Utilize the designer's bias for action to test something out and create a prototype that you can learn from. Your beginning point for creating experiences that will support the new viewpoint derived from the aforementioned point is the new perspective itself. By doing this, you recognize a circumstance at work where you can provide value to yourself or your workplace and then take appropriate action. Send two or three coworkers from whom you wish to learn anything an email, for instance, asking them to get together for coffee or a talk.

Choose tiny, doable actions. You prioritize them at work.

Let's assume you're feeling disconnected at work, so you make a list of folks you may visit each morning or invite to lunch. If you're feeling unmotivated and tired, take a daily walk and treat yourself to a decent coffee.

This may be plenty for now. If you want to take this procedure further, use Burnett and Evans' internet tools and frameworks.

Developing the daily practice of reframing

“We’re not discontented kids in the backseat of the family minivan, but how many of us live our lives, especially our work lives, as if we are?” — Bill Burnett and Dave Evans

I choose the good enough for me perspective every day, often. No quick fix. Am a failing? Maybe a little bit, but I like to think of it more as building muscle.

This way, every time I tell myself it's ok, I hear you. For now, that muscle gets stronger.

Hopefully, reframing will become so natural for us that it will become a habit, and not a technique anymore.

If you feel like you’re stuck in your career or at work, the reframe of Good enough, for now, might be valuable, so just go ahead and try it out right now.

And while you’re playing with this, why not think of other areas of your life too, like your relationships, where you live — even your writing, and see if you can feel a shift?