Features, Products and Platforms

Case Study: Popular Poker Thought Leader 'Chicago Joey'

Rachel Thinks Series

Joe Ingram (Twitter @joeingram1) is a highly popular and well regarded voice in the poker industry. He goes by “Chicago Joey” or “Papi” or simply “Joey” to his many fans. He is best known for his unique style of covering topics and events in the poker world.

Joey (as I prefer to call him; feels more friendly) does very long, extended interviews with popular characters in poker. He leans toward an investigative style. Over the years, it is quite clear that he spends a lot of time on understanding his audience.

It is also immediately obvious that the man behind the videos takes great pride in nurturing and growing his main social media channels or vehicles in the right way. No matter how many years a person spends trying to grow a meaningful presence on social media (or the Internet more broadly), you cannot get to his level of reach and influence without dedication, commitment, and (above all) tremendous skills.

I thought about Joey when thinking through the differences between: Features, Products, and Platforms. At the individual level, I think most people do not think twice about the topic of product form factors and architecture.

In technology, strategists are consumed by the similarities and differences among the three types of value delivery. So, I thought it would be quite interesting to apply the concepts to someone many readers can relate to. If you are not familiar with Joey or poker, you can just swap out his name for your favorite thought leader in another domain/industry. Or, perhaps you can even swap yourself into the case study.

Grounding on the Terms

Before we get into Joey, let’s briefly define each of the three ways a product can be delivered. By product, it is anything you make or create and sell or give away.

A product is anything that is created and packaged for someone to consume in order to derive or gain value. Within the product, there are features that trigger functionality to be able to deliver that value through consumption.

This tricks us into thinking that the product is at the bottom (starting point) of the hierarchy. In fact, however, the feature(s) are the lowest point in the hierarchy.

Above the feature rests the product. The smartphone is a good example. The camera functionality has multiple features. And, those features are part of the product (i.e., smartphone). In turn, the smartphone (product) can serve as both a standalone product or part of an overall, larger Apple ecosystem (platform).

When we use the camera (feature) to take a picture using the smartphone (product) and sync with iCloud (platform) we are effectively using the smartphone as a “feature” of the platform. This gives you a clearer sense of the hierarchy as one subsumes the other as you evolve from one to the other.

This leads us to the three (3) main characteristics of a true platform:

A platform must be extensible, modular, and interoperable.

Extensible means the platform does not just grow upward (e.g., more users). The platform must be flexible enough to add changes and new capabilities - sometimes by other systems (products or platforms). The base extends outward.

Modularity means the platform is constructed in such a way that people can consume parts of the whole without disrupting the totality of the platform. A crude example would be using a smartphone only for the camera and picture filtering app.

Interoperable means that the platform is able to exchange information and communicate with other systems in a seamless or smooth manner.

You can see right away why the dominant technology companies relish the idea of becoming or remaining a platform. It should be added that the most powerful platforms must have — in addition to the three traits listed above — two levers that enable dominance.

A dominant platform requires a high level of (a) seeding and (b) control or governance.

The seeding is referring to users while the control refers to the platform being core to the ecosystem that builds around it. The Windows platform has almost total control while the Linux platform has limited control. This is due to the presence or lack of control over the core. The seeding, of course, allows for fast growth (i.e., a packed restaurant attracts diners) but also makes it hard to move away to another competing platform.

Individual Level Platforms and Fractals

So, how is any of this relevant to the individual? Plenty. The company is but a fractal of the individual. Fractals are objects that look similar across an extended range of sizes. Think of snow flakes or networks of rivers. The shape at a large size or scale looks the same when you drill down or zoom into smaller and smaller sizes.

Many things that work at the company-level also work (or applies) at the unit or individual level. This is where the Joey examples come in.

The Product That Is Ready To Transform Into A Platform

Joey Ingrams online presence is a product waiting to become a pure platform. It is not yet a platform because it is a product within the (for example) YouTube platform. It is not a feature since the product has taken over the features.

If Joey’s product were merely a feature, we would just do something with it and stop there. Let’s say he creates and publishes a video on the topic of online bots cheating on a poker site. If I only go to his online property(-ies) for that kind of information, he is a feature as I would only derive value from that single feature.

However, I seek out his multiple properties for a variety of reasons. I consume news, tips, entertainment, gossip, investigative outings, and broad perspectives. Each of these “features” make Joey Ingram the “product” to satisfy the portion of my life that is interested in an industry (e.g., poker).

How do I consume those things? Joey on YouTube is a product. Joey on Instagram is a product. Joey on Twitter is a product. Joey on podcast players is a product. To have multiple products he needs multiple form factors for delivery and consumption. And, he has those multi-channels of distribution for selective consumption.

Why Isn’t Joey a Platform (Yet)?

Now, let’s go back and review one by one all of the necessary pieces to become a true platform.

Does Joey’s product have seeding? Absolutely. He has a very large fan base. It may seem small compared to celebrities or thought leaders in other much larger industries. But, on a relative basis, Joey has a significant following and loyal fan base.

Does Joey’s product have core control? I would argue that he has some degree of control or governance characteristics. A rogue or bad actor app developer would get kicked out of the entire Apple ecosystem or platform. But, the harmful person in Joey’s (product) community can only be fenced out to a degree but not entirely removed. So, there is some level of control but not enough for it to be thought of as “core control.”

Is Joey’s product extensible? So far, it is not extensible. The products feed one another but remain relative confined to a finite set of demographics largely centering on poker players. Of course, this was by design as he gave birth to his online brand and products via his passion for all things poker related.

His products can grow upward (more poker users) at the moment but does not extend into other domains. Therefore, it cannot expand the addressable market of content consumers. This presents a great future opportunity. The Joey (poker) product being extensible means that a newly added Joey product (general risk/cheating in mainstream public) will be a purely additive play .

Then, his product becomes closer to a platform by easily extending out the base East/West instead of just North.

Is Joey’s product modular? Actually, I think his products are modular in both function and purpose. It is possible to de-couple parts of the whole and consume those parts without struggle. There is plenty of opportunities here, as well. Right now, the modules are very similar or heavily skewed in one direction.

Modularity involves the ease with which categories are grouped and tailored. If I can take cheating investigations (category) and consume it through my podcast player (tailor the delivery), the modularity litmus test is met. Now, there has to be enough volume (content) and not just seeding (users) to make this a critical part of a platform. Again, a potential for massive future growth.

Finally, is Joey’s product interoperable? This one is a ‘no., not yet but shows some signs of it.’ At a human level, Joey is interoperable. He can seamlessly exchange data or information with another platform player or influencer. For example, Joey (poker and risk expert) and Nasim Taleb (statistician and risk analyst) getting their ‘platforms’ together to discuss the risks of sports betting legalization on the future of ticket prices for families.

As you can see, this cannot happen today because Joey’s product would get subsumed by Nasim’s larger product or platform. If Nasim is product then Joey becomes a feature within that product (book, podcast, article, speaking panel, etc.). If Nasim is a platform, Joey becomes a product within that platform (i.e., Joey loses control and the user traffic would go from Joey to Nasim). This occurs due to the nature of platform control and governance.

Opportunity Is Gigantic

If you have been paying close attention to this point, the conclusion I am drawing should be very clear. Joey is in an enviable position right now.

The pessimist would say that he is a big fish in a small pond. That he is a niche influencer. The pessimist would know nothing about how the interplay of products and platforms work in technology.

If you are ‘old school’ or do not understand technology strategy, you would see things through the prism of population, end user affinities, and content specialization. That is, you view the world through limitations.

If you believe in the concepts of flywheels, network effects, and platforms, you will view things through opportunities. You do not get limited by specialty scale (small) but start to view things through global-scale (massive) because it becomes clear that those who seed the platforms do most of the work once you enable them to do so.

In Closing

Not all of us are lucky to have Joey’s fan base. But, it took endless hours and several years of near obsessive work for Joey to come this far. As he has stated many times, he never placed importance on the business aspects of what he was doing. I can only imagine the potential once he does.

Joey has always used his following to convert a fraction of them into affiliate earnings. In my opinion, he has done this very carefully and selectively because he kept his eye on the long game. If he were short sighted, he would have burned his seed before it can grow into what it is today. Soon, it may be time for his seeds to become affiliates for Joey’s platform. That is how the product becomes the platform.

But, we do not have to have Joey’s large online presence to apply the main tenets of this article. For any individual or group business, it is beneficial to draw out or map your strategy as a journey from: Feature to Product to Platform. You can do this with jobs/careers, podcasting, blogging, selling, and just about any other business endeavors - including poker. Some poker pros are a feature. Most are products. And a few are actually platforms.

Find and follow me on Twitter @rachelees69.

The Paid Option and Me

The Roots of This Newsletter

Rachel Thinks Series

This newsletter has a paid subscriber option. Anyone can sign up to receive free articles, though. To date, almost every article has been free. To explain why I even have the paid option I have to go back in time and describe the origins of “Rachel Lees.” This is that story.

For those not interested in the extended story, here is the summary of why I have a Paid Subscriber option:

My long form articles require dedicated time to publish. This time is valuable to me as a semi-retired consultant who still works with clients. Further, I have a family that a majority of my time is consumed by and, of course, also have personal obligations. I view the paid subscriptions as a good way for an exchange of value.

Readers can opt to support my writing (i.e., time, effort, and uniquely unfiltered) and, in exchange, I can devote the required time to share my experiences, knowledge, and views on various subjects/topics that will help people get attracted to technology startups. Technology startups have changed my life in a positive way. So, in the end, the paid subscribers are my “power” readers who give me the necessary motivation to write for the long haul.

Why Rachel Lees?

Long before I created a Twitter handle under the pseudonym “Rachel Lees,” I had a YouTube account with the same name. As a lifelong tech industry professional, I have always limited my online footprint for several reasons. Poker is a hobby of mine. I get just as much enjoyment from watching poker as I do from playing the game.

Poker is an escape for me in a lot of ways. So, I created the account to consolidate all things related to poker. In the beginning, I pretty much just watched a lot of poker videos. Poker live streams such as Live At The Bike, Poker On The Strip, and Poker Night In America were some of the shows I regularly watched.

Soon, I discovered vloggers such as Andrew Neeme, Brad Owen, and others. Then, I started to enjoy watching Joe Ingram’s video interviews. Next, I found poker podcasts. I was spending almost all of my free time being entertained by poker.

Without much thought, I figured that Twitter would help me reduce the amount of time I was sinking into poker while still managing to get enough highlights. It turned out that there are a lot of “Rachel Lees” in the world (go figure). I added the “69” to my name because it was a birth year of a sibling that I knew would be easiest for me to memorize.

After roughly 25 years in tech as a “more technical than average” fan of new services and products, you can imagine the sheer amount of online accounts and log-ins I have … it is a ton.

Twitter ‘Rachel’ Is Born

Once I got onto Twitter with this pseudonym handle, several unexpected things started to happen. I got more and more interested in the people I was watching on streams and videos. I started to learn more about these people in articles. But, most importantly, I read and followed them on Twitter and got a better sense of who they really were. It helped that I knew some of them in real life.

Second, I became fascinated with the business aspects of the poker industry. As a longtime operations executive, most things that my brain processes get instantly modeled in terms of business operations, economics, and motivations (or, incentives). This makes something I am passionate about that much more intriguing. But, it also means (unfortunately) that the stupid shit rings alarm bells quickly and deeply.

Third, the whole social behavior aspects of poker Twitter got me deeply engaged. Poker twitter is a highly advanced lab experiment in that it is a pure playing field. Poker players are individual contractors or self employed business entities. Most people are beholden to no one. Of course, some of the more prominent names are nothing more than employees to operator businesses. And, some are chained to longtime friends they owe a debt of money, gratitude, or loyalty to …

But, overall, poker Twitter is comprised of individuals who are anti-establishment and proponents of freedom of thought and expression. Contrast this with other fields where people are highly protective of their artificially created reputations.

In other fields, many people are on Twitter with a selfish agenda. They also are risk averse and thus, calculated, sanitized, and filtered. In poker twitter, generally speaking, people have a much lower incentive to be selfish. The incentive to share and debate is much more pronounced.

Remaining Anonymous

The option to reveal my true identity was never an option. While I am not famous or infamous, I am a highly recognized (and, honestly, a well respected) “lifer” in the part of the tech industry where I have led prominent companies and teams for the last 15+ years of my ~25 year career. I just do not need the unnecessary drama.

I will not get into the risk:reward calculations openly but you can take my word for it. I did not take these decisions lightly. I poured a lot of time and thought into remaining anonymous or starting over with my identity. Over time, I have written so many tweetstorms, tweets, and long form articles that I decided that my identity does not matter. People have more than enough data to judge for themselves.

There are many downsides when writing under a pseudonym. The obvious one is that it is very hard to build a following due to the lack of trust. Not so much who I am (although there are some obsessed people who only want to know that), but trust that what I share is actionable, informative, and accurate.

I am, after all, writing as a subject matter expert and sharing my knowledge base liberally. With time, that obstacle has been removed as people will make up their own mind given the track record and substance of what I produce.

The second downside is that I have to fight the urge to not be a bad actor. Meaning, I get tempted daily to call out bullshit when I see people I know in real life (mostly VCs, company and startup executives, and some poker pros/players) absolutely write horseshit manure-like lies or twisted ‘truths.’ Really bad people who have masterfully deceived the masses on social media.

I have put in a lot of effort not to go after them. Why? Doing so would be easy but the repercussions are bad. The intent and substance of my writing will be overshadowed. People will falsely believe I am nameless in order to attack others under the cover of anonymity. Pretty cowardly. And, on a personal level, I do not want to waste time reacting to others. Much of my writing is based on my life in business and daily thoughts.

Any Upside To Being Anonymous?

There is a big upside to writing under a pseudonym. In my world, as in many, people are always selling, marketing, and promoting themselves. There are two camps of people. Those who are busy doing the work. And, those who write about the work or how to do the work. Those who are doing the work at a world class level simply do not share or write publicly. This is something I know first hand and not debatable in my mind.

But, like anyone else, I read a lot of materials. Most of the things that are written about the startup world, technology business (operations side), and the players who drive it are pure garbage. They either get the story or facts wrong or recycle already known intelligence over and over. Or, worse, they are so deeply sanitized and generic that they are safe to write and consume but totally useless to someone who is on the outside but looking to jump into tech.

By remaining anonymous, coupled with curated insider knowledge and experience, I felt that there was room for someone like me to make a unique contribution to the “state of art” (i.e., knowledge base). My logic is that since I have no personal agenda in either direction (to benefit nor suffer loss), it is a disciplined way to write with raw ingredients and let others do the cooking. In an odd way, being anonymous frees me to be more controlled while being open.

The Newsletter

The Rachel Lees Thinks newsletter was started without much of a plan. More than anything, the newsletter gave me the ability to write long form articles. On Twitter, I used to write these very long tweetstorms. I concluded that it was a waste of time because of the way Twitter works. Those tweetstorms just get a snapshot exposure then get buried for eternity.

It just made no sense to keep writing long tweetstorms. So, I thought about blogging but that would mean that I actually work on building an audience for the blog. So, one day, I thought to myself the following:

Increasingly, I’m learning that there is a small audience on poker Twitter that enjoys my writing and sharing. I have proof in the metrics. With such a tiny, miniscule following (which I spend zero time trying to grow) the engagement level is relatively high. I think many people would benefit from seeing that they have real options outside of poker. But, I can also see from what I’m reading that they are getting very bad advice.

And, they are getting bad advice mainly because they are getting plenty of self-serving, biased advice. It is like watching a bird caged and fed artificial sweeteners. The career path outside of poker is vilified while the poker life is glorified. I felt this was harmful to some people. Thus, let me see if my alternate message resonates with a handful of people who are open to the idea of having go-forward options.

Instead of forcing my views on others, let me see if I can do my part to help prepare them for an uncertain future.

Around 6-7 weeks ago, my messaging and approach got tuned toward this goal. I no longer spent much time pointing out stupidity. Instead, I started to write to illuminate contrasting realities in both fields. I wrote guidelines, best practices, and tip pieces with occasional reminders and reinforcements. And, above all, I began to write as a historian would if they had walked the journey instead of just observing it for documentation.

My Target Segments

Over the weeks, it became clear to me who I was writing for - or, serving - and who I was not writing for. My writing is not for 90 percent of the poker pro/player public. My writing is for less than 10 percent (maybe even less than 5 percent) of my feed followers who fall into one of the following categories:

(A) Young poker pros who got into poker because they did not feel like other options were available at the time but have since changed their outlook or future plans;

(B) People who are in tech jobs but play poker as a recreation or hobby;

(C) Business operators (e.g., small LLC to self employed) who want simple, straightforward operations advice (e.g., marketing, sales, strategy, finance, and comprehensive management) from someone who knows the subject while caring about their success (I am, after all, a customer of theirs as a “power” consumer of all things poker).

(D) Older people who are in non-tech careers but feel that technology has become an increasingly relevant aspect of their later stage careers and want fresh, new perspectives.

I did spend a lot of time figuring out my goal and objectives. You can see it reflected in the topics I select for the newsletter. Why a career in tech startups is not only rewarding but also a practical option. And, my objective is to continually explain aspects of the tech industry so that the reader will gradually learn more. Which, then, enables people to feel confident that this is something worth spending and committing serious time, energy, and resources to pursue.

For the people already in tech who play poker, the articles I focus on have a lot to do with managing one’s career, accelerating career growth, and juggling the two passions (tech and poker) without losing sight of priorities.

If we ever reach “C” and “D” then terrific! But, I am not anticipating that to happen. If it does, then great. It is hard to serve all four categories of readers even if the current makeup appear that way. But, one thing is (or should be) very clear …

Money Or Growth Ain’t Goals

If money were the goal, I would not spend precious free time to devote to this newsletter or even to Twitter. There is no ROI in spending time publicly as an anonymous persona. No amount of money I would attract from this activity would ever get me remotely close to break even.

Trolls appear to get some ROI in terms of gratification at attacking or attempting to harm others. I get no such joy and limit it to extreme cases. I prefer to think, write, share, and respond. Almost all replies to my writing or Twitter posts get a response from me - as long as it is thoughtful, funny, or adds to the conversation.

Money is a non factor. If I wanted to make any amount of meaningful money from this project, I should actually kill the project. I would make more money by taking more naps. As it is, I am losing money with each minute and hour I spend writing this stuff.

If growth were the goal, I would do things exactly the opposite of how I am approaching my newsletter - and even Twitter account. I would spend money upfront to acquire a large base and prune it in a top-down manner. Then, I would charge money and keep expanding that base.

Why Even Have a Paid Subscriber Option?

I chose Substack because of the integrated platform that allows me to write but also experiment. This platform makes it remarkably easy to stand up a content marketing experiment quickly. It integrates a few key components into a single, simple platform. A big component is the payment piece. They handle all of the complexities inherent in payments.

Ironically, if the paid subscriber numbers get too large, it no longer makes sense to remain on this platform as the fees (10%) would balloon. I am not worried about that for now, though. The ‘ease of use’ value I’m getting right now from the service is enough.

I should note, however, that so far I have not seen any benefits beyond the integrated portion. This site does nothing to bring new readers into your newsletter. They do it only for the largest newsletters - which also happen to be the ones that do not need the help.

So, as an invisible nobody, I had to start from literal ground zero. My mailing list had zero contacts in it. I just wrote my first article and posted it as a tweet on Twitter.

Then, a weird thing happened. People started signing up. Then, people started signing up for the Paid Subscriber option. And, they often purchased the annual member option. I must not have had more than 2-3 articles posted at that time. This led to a couple things on my end.

First, it triggered an extrinsic motivation to think more thoughtfully about the subjects to pick and write about. The paid subscribers became like customers. And, second, it also sparked an intrinsic motivation and got me pretty excited.

For me, it turns out that while there is no payback for the amount I am investing into this writing (in terms of lost hours) there is a definite ROI. On most days, I actually look forward to clearing my calendar and writing.

The paid subscribers give me the motivation. It surprised me how strong this dynamic had on my thoughts, emotions, and behaviors.

Future Decisions or Direction

I’m still sorting through this part. A large enough portion of the readership are paying subscribers so I can’t leave all the articles free forever. There is a commentary and discussion feature that only paid subscribers have access to … so, I’ll probably want to activate that capability at some point.

On the other hand, I do want some articles to be accessible to anyone. Right now, my thought is to keep free the most widely relevant articles. And gradually write more and more articles for the paid subscribers so it does, in fact, become a genuine value exchange.

My fear is not losing free sign ups. The numbers are so low in the scheme of things that losing readers is not a concern. Right now, I am strictly focused on (a) what will continue to motivate me to write without losing sight of the integrity (quality, experience-based candor) and uniqueness (unfiltered) of RLT and (b) how do I serve the readers the best way. It is not as simple as I thought it would be.

What About Rachel Lees?

It is odd to do a self Q&A but who gives a shit. Here are some of the repetitive questions I have gotten on Twitter through the feed or DMs (which I really do not like outside of a handful of people).

Q: Why did you select the name Rachel Lees?

A: I have no idea. I always liked the name Rachel and, at the time, I was reading an article about the Civil War and had the name Robert E. Lee on my mind. The surname Lee happens to be common in Asia so it was impossible to create accounts under that surname. So, similar to Lands’ End, I just tried adding the ‘s’ but it turned out that there are many people named Rachel Lees IRL so I had to add the ‘69’ to get unique accounts approved. As I mentioned at the start of this piece, the ‘69’ is a birth year (not of me) that I could remember easily.

Q: Why won’t you confirm that you are or are not female?

A: No one will believe me either way. I tend not to bother with things that won’t matter. People can and will judge me for the substance of my thoughts as delivered through the written form. If my gender matters to a person (or reader), those are people I would rather not have reading my material anyway.

Q: Why do I not follow back?

A: Two reasons. I do not want DMs. And, I can’t manage my own Home Feed when I follow a lot of people because I’m a voracious reader of original post tweets from a very diverse range of people. So, I use many Lists instead to be able to switch back and forth between categories of Twitter users. If you follow me, you’re likely on one or more of my Lists. I don’t pay attention to follow and follower counts. If I follow someone, it is because they tweet very frequently. Most people tweet at a low volume or retweet at a high volume … and I do not want those filling up my home feed.

Q: Why are your tweets all over the map?

A: I get this complaint from time to time. I keep a personal editorial calendar for my newsletter which I have posted in the past. But, for my main twitter account, I just tweet what I feel like expressing. Again, I am not trying to build a following. I don’t want to put any energy into tweeting what will get likes or engagement. I don’t play up my gender or play it down. Almost all of my tweets are just thoughts I have in my head.

Q: Are you an angry person in real life?

A: What you see online is what I am IRL. If you read what I wrote sporadically or selectively then, yeah, I guess it’s fathomable that you will think I am an “angry” person. But, if you have read everything or regularly kept up, I’d find it difficult to imagine that anyone would characterize me as an angry person. But, I am pretty intolerant of imbeciles and bad people both online and IRL. I am also highly intolerant of mediocre performers in a work or business context.

Q: How do you find time for the high volume writing?

A: I am a very busy person. Fortunately, I have a few things going for me. I run my own firm now. I answer to no one and have a life/work set up whereby I can control the flow of work and the types of work. My day is not a continual set of hours that are inter-dependent. I have large blocks of time that I proactively set aside. When I tweet short missives, I can be awakening from a short nap or dosing off in a two hour meeting with bozos.

I’m also somewhat OCD in that I love to read clever or thoughtful tweets or articles … and cannot stop once I start. I have gotten a lot better by not reading as much as I used to. I don’t selectively read tweets from “friends” or "people who I need to “look good to.” That’s a big benefit of being a nobody. I like what I like and ignore what I don’t like.

Also, I think very slowly but write very fast. I am not a good writer but I am an extremely fast writer. I think this happens at both work and on social media because I do not frequently need or use source material. I write when my 25 years of “on the ground” experience serves as my source material. This lets me write very fast and somewhat detailed materials at the same time. The stuff on the economy, think tanks, and political economics from a few months ago did take me a lot of time. I do not know enough about those things as many others so I had to do a lot of research and write in a more conventional way.

Q: Are you a crazy person?

A: No, I don’t think so. I’m pretty self aware so I can see why more than one person would ask me this question. There have been times that I have come across as unstable - especially when going after organized crime leaders in poker or some asshole poker pro. I just chalk it up to a swelled up feeling of frustration of not being able to roast them without revealing my identity. There are times (though rare) when I just want to post factual evidence and grill a bad person but … I have to bite down on the tongue and get cryptic with my messages. I realized that this behavior only made me look nuts so I stopped doing it.

Q: Your politics tweets have all but disappeared. Why?

A: Around a month ago when I decided to launch the newsletter I just decided that anything politics related made me sad and depressed. It left me in a funky mood that was not healthy for writing.

Q: Is what you’re doing deliberate or random? Is there an end goal to any of what you’re doing?

A: It is not random. Some time from now, you will see a major transformation and disruption take place in the world of recruitment. Expect to see LinkedIn and hundreds of other job sites and services become obsolete overnight. Be on the lookout for someone to turn a new model into a manual reality via Petri dish then into a scalable, productized YaaS (aka SaaS) platform that transforms the $153.5 BILLION recruiting and staffing market in the U.S. alone.

Rachel Puts On Sales Hat

As for the paid subscription, most of you won’t need or want to do it. But, if you do consider it, view it as buying me a salad and lemonade each month as your way of letting me know you got value from the newsletter. It really does motivate the writer. And, I will continue to write for you as my thanks in exchange.

I do understand that if you compare it to, say, Netflix … Netflix provides 1000x more entertainment and value.

Note: Also, my understanding from Substack is that free or public articles are theirs to keep even after writers delete their account or leave/move away from the platform. That is a small but relevant factor, as well.

That’s all folks … for now!

Find and follow me on Twitter @rachelees69.

The Asshole Boss Turnaround

Development vs. Management

Personal Development Series

For a more comprehensive look into how and why bosses become assholes, Bob Sutton has a great book called The No Asshole Rule. I read the book when it was published in 2007 and it is a very good book.

Instead of regurgitating the book, I want to share my own journey from normal worker bee to people manager to executive. And, how I went through the full cycle of turning into a jerk, then asshole, before reforming into a good non-asshole leader.

The Early Years

Like most people, I was a conventional employee. I put in massively long hours at work. In terms of behavior, though, I was like everyone else. I expected to be treated fairly and, in turn, I always made sure that I treated others fairly. I was an individual contributor or IC for a couple years.

By circumstance, I wound up managing another person at a young age. I think I must have been 26 or 27 years old. The job was to split up our work so there wasn’t too much supervising responsibilities. We were more peers than anything else.

My first real managerial job in tech came 3-4 years later when I was 30 years old. It was a small team of six people (including me). A couple of them were older than me and the others were around the same age.

This was a full people manager role but I also had to do the work. I guess we would call this a “player coach” type of position.

Studying How To Be An Effective People Manager

No one really knows how to manage someone else. You can read books and solicit advice from long time people managers but it won’t help much. Much of the job is reacting to things that happen day to day and even hour to hour.

As a junior manager, my staff did not seek my approval on stuff but, rather, they came to me when things were broken. They brought problems and offloaded them to me. “You’re the boss,” they said. And, there were numerous times I thought, “This is not what I imagined being a boss would be like. This sucks.”

I read some books to become a better manager. My assumption was that my job sucked because I was a bad manager. It was at this time that I read Andy Grove’s famous book, High Output Management. You can read this nice summary of the book review HERE.

Reading the book did not help me much. I quickly forgot all of the invaluable lessons given in the book and soon returned to my people management hell. These were pretty frustrating years.

Growth Forces Growth

Looking back at those years, I was definitely not ready to manage other people. I was what you would call a “rising star” or alpha dog. I rode up the "corporate ladder” AND startup food chain very quickly. This is highly unusual even in tech where some of the smartest, most ambitious people gather.

To make matters worse, I was doing the tech thing in the epicenter for ‘type A’ personalities, Silicon Valley, and doing it at the height of the “Internet bubble.”

A startup’s fate is pretty much dependent on 10 percent or less of the workforce. Yes, everyone in the company contributes and makes it possible for the 10 percent to focus on the critical things. But, anyone who has ever been a part of an insanely successful startup will tell you this is absolutely true. Not everyone contributes equally. The differences are very pronounced.

It was common for the CEO to ask other department’s VPs to meet with me for my thoughts and input. My ego got awakened and this is never a good thing early on in one’s career. My work touched every corner of the business. And, it felt good but I was also emotionally and mentally spent by midweek.

As our startup picked up momentum, we got a large funding round secured. The company went on a hiring spree and we doubled headcount to 150+ people within 8-9 months. My VP told me that I had no choice but to start managing people. By that, he meant that I had to do it right.

I hated the idea of managing people. I told my boss that it would just slow me down and we would suffer as a consequence. He would not hear any of it. There was no way he would carry over a dozen direct reports.

Resentment Builds Up

I was given a title and pay promotion to Director. A Director job in tech is a very big deal. Unlike other industries, tech company’s very rarely give out the VP title to people. This is partly why companies have been doling out “Head of X” job titles. Almost all of these “Head of X” jobs are Director or Managers in the HR system.

Banks and investment firms pretty much give half the staff a VP title. It means very little. In tech, the VP is almost always the top executive of a department or function who sits on the executive management team. In larger tech companies, there is some VP title proliferation but they all have VP responsibilities.

As such, some people spend a decade in tech before becoming even a Director. So, it felt good to become a Director-level member of the team but I did not want to manage a team.

Even back in those years, I had a habit of reducing everything down to its logical end result. And, in my mind, managing a team would reduce me to the lowest common denominator. I had not learned the power of leading teams, yet. During these years, I viewed the team as a big burden. A heavy baggage that kept me from going faster.

To make matters worse, I inherited these people from my VP so that did not help matters. Every time a bad situation came up, my first instinct was not to fix the issue but go back into my office and fret. Why do I always have to pick up after these people. They are all getting paid a lot of money.

They all went to elite Ivy League schools. But, why are they so mediocre? Why do they seemingly not care as much as me? Why do I have to hold their hand across the finish line?

What the hell is going on here? That was pretty much the thought that lived full time inside my head. Coupled with my growing ego (as the senior execs were still relying on my regular inputs and suggestions) and frustration at spending countless hours on problems, my inner resentment was building up.

The Jerk Years

I look back at those early years as a Director-level manager as the Jerk Years. I was not an asshole (yet) but headed in that direction. At the time, however, I thought I was a great manager. How could someone everyone considered one of the stars of the company not also be a star manager?

The first sign of being a jerk is to manage up all the time. Since the execs often relied on me or pulled me into major decisions or projects, I was increasingly managing up. And, when you manage up a lot, you wind up looking down at your own team. Everything starts to look like a vertical structure.

My team treated me with outward respect but I learned later on that they fluctuated from fearing me and loathing me. Even startups have 360 degree reviews sometimes and, unfortunately for me, I learned this reality through my own 360 management feedback report. My face turned red but not due to embarrassment - it made me angry.

How dare these mediocre people criticize me?

Escalation Into An Asshole

The transition from merely being a jerk to becoming a full blown asshole does not take long. Give a jerk some real authority and s/he will become an asshole. Up to this point, I managed people and had my own independent work. But, my VP did all the other things such as making final decisions on big things and owning the strategy as well as full budget.

Our startup kept growing rapidly. My VP took on another department that needed his deep experience, maturity, and savvy while I was made the VP of our group. I was in my early 30s. I remember thinking that everyone was lucky to have me as a boss.

A department is only as strong as its VP. This applies in every company. You may love your boss and get along great but if s/he is not strong, your team will not get its share of resources much less get prioritized. Who was more respected than me? No one.

It turns out that everyone started updating their resumes. That’s right. Here we are as one of the hottest startups in Silicon Valley and my medium sized team was preparing to head for the doors. I had an executive assistant and this is what she shared with me. That is one of the benefits of having an EA. They are in the loop on almost all office related gossip.

Identifying the Asshole

Here are some of the things my team brought up when I asked them to provide me direct feedback.

Always spent time with other executives and not enough with the team.

Afraid to bring problems to me because I always got upset.

Terrified to make mistakes since I was so detail oriented.

Expectations were unrealistic and demands were too high.

Rarely explained thinking process or decisions fully.

Always looked impatient and hurried discussions in one-on-one meetings.

Those are just the ones I remember after all of these years. The list was endless. I still have the notebook from those early staff meetings. The pages contain very little note taking. Just a lot of words and phrases that bring back my emotions. Everyone hated me and, for once, I started to believe that they had every reason to despise me.

The Bob Sutton book on assholes in the workplace had not been written, yet. I did the next best thing and asked my former boss what to do. He was what we call a “silver hair” and had a limitless amount of experience managing and leading people.

He asked me why I thought I was an asshole. I rattled off all the reasons my team cited. And, I remember my former boss getting visibly frustrated. He asked me for my reasons - not theirs.

I told him that it was probably because I had higher standards and they were not living up to them. He told me that this was the one thing that was likely not to be true. He taught me a valuable lesson that day.

My former boss asked me if I wanted to do anything about the grievances from my team. He asked me to step out of my own skin and view the situation as any other business problem. Instinctively, I assumed these were all flaws in my people management skills. He taught me that they were my personal flaws.

Over the next few days he and I painstakingly went over everything on a whiteboard. I am a very diagram reliant person. I can listen to a lecture or speech but not recall any of it. But, if I see something written or drawn, I will understand it and remember.

Relationship Dynamic

A manager becomes an asshole not by how s/he behaves but by the way they view themselves. The moment you think that you are better than others — hence, why you are chosen as the VP of the department — you are already showing asshole tendencies.

Many people have cited the Peter principle which says that:

“… people in a hierarchy tend to rise to their ‘level of incompetence.’ In other words, an employee is promoted based on their success in previous jobs until they reach a level at which they are no longer competent, as skills in one job does not necessarily translate to another.”

I am not a big believer in this popular belief. In tech (especially startups), people are promoted based on doing the next job exceptionally well. This happens due to resource constraints and the velocity of the firm’s life cycle. As for the inability to scale problem, those definitely do exist.

Later on, I discovered this when closely leading dozens of highly focused, specialized professionals and overseeing the many thousands of people around the world who were, in turn, let by them. The skills required to do this job at a world-class level are vastly different than the skills required to perform a startup CEO job.

But, on the whole, managing a team of five (5) vs. 50 are not very different. That is, the skills translate fine and the competence problems are not only overblown but mostly non-existent.

Results Open My Eyes (and Mind)

After several hours of interrogating me, my former boss distilled things down to a few key observations. He knew me as well as anyone in the workplace so I gave him the benefit of the doubt.

He pointed out some new things that my own team’s feedback did not contain. Or, at least, things were framed differently. It was all about how my own thoughts were serving as hurdles. The same thoughts that propelled me to be a star were inhibiting me when trying to propel others.

I had spent very little time understanding how my team learned and worked.

There was no margin for error built in to anything. This led me to anticipate problems.

My pace demands were suboptimal. I needed to explain things to get full commitment up front.

And, I was not working through the average of the team but rather expecting everyone to catch up to the top performance.

Basically, I was irrational and unrealistic in the way I handled my team. The biggest lesson for me was that I was also unrealistic with myself. I had gotten by (and even been rewarded) with this attitude and approach for so long that I was blinded by my flaws.

He taught me an important lesson that week that I remember to this day because I would teach it to all of my future people managers. And, it was this …

Bad bosses view their team as a finished product. They are either performing great or not. Great bosses view their team as an ongoing development project. They are all capable of performing great but need help to get on and stay on the high performer track.

This simple advice sounds almost too obvious for it to matter. But, for me, it changed the rest of my management career. I no longer feared looking bad because my team under performed. I no longer felt frustrated at having to explain things in excruciating detail - often, several times over. I no longer got mad that someone would send me a shitty draft and feel perfectly fine going home at 5pm.

You see … bosses are assholes not when they are selfish. We are all selfish to varying degrees. In my mind, bosses are assholes when they are driven by fear. They become top executives by not just being high performers but exceptional performers. Relinquishing control to a team frightens people. You are put “in charge” but in many ways you feel like you are “losing control.”

And, all of this bad stuff washes away when you make that simple change. You are developing people and the work will never be finished.

People Development vs. People Management

The duty of developing people is not the job of the HR department. Developing people is not even the job of a team manager. A team manager’s job is to get teams to execute and deliver expected results. But, the job of a VP is to develop the people.

A lot of new executives get lost during their first couple years as the top functional or business head. I know how this feels. There is a strong temptation to either be (a) popular with everyone or (b) respected by everyone. People often fall into these extremes.

They take Andy Grove’s lessons literally and become entranced by the processes, procedures, and playbook type of management overhead. That is, they become like objective-driven robots (i.e., a more humane version of the command and control disciplinarian). Or, they turn into a popularity contestant and get run over by their own team.

Culture/Behavior vs. Expectations/Standards

By nature and design, a tech startup has a high level of uncertainty and ambiguity. A lot of processes are missing because things are moving fast and the firm is facing daily crisis. In this type of environment, your people are developed by values and behavior.

You can't fake it. It becomes easily noticeable whether you are trying to develop the team or to manage (control) the situation.

When a startup reaches Series C or D, you will need to gradually transition into setting high expectations to drive performance improvements. Culture or behavior won’t be enough. This occurs because as the team grows, lingering uncertainty and ambiguity will kill off all of the gains that come from individual development.

Defining roles and responsibilities. Setting objectives and metrics. Weekly reviews. All of these things become a core part of the people development work. Remember that people development never stops - it is the foundation upon which expectations are layered atop.

Closing Thoughts

There are many reasons why a boss becomes an asshole. So many reasons, in fact, that books are written about it. But, if you reversed all of those reasons (e.g., micromanaging people) the asshole will largely remain an asshole. And, this is because the foundation is set wrong. They are managing vs. developing.

A budget is managed. Work is directed. People are developed. This sounds simple but it is an excruciatingly hard thing to switch.

The asshole boss virus strikes people who are blind to the stark difference between Development vs. Management. The moment you are able to look through the prism of People Development, everything changes in terms of how you think, act, work, and manage.

Asshole bosses think … “We will succeed because of me. We will fail because of them.”

Great bosses think … “I will succeed in developing my team. We will succeed because of them.”

As you can see, these two management views are completely different. Once I woke up to this, the rest of my years leading teams and companies not only became rewarding but damn enjoyable. And, today, as I sit here reflecting … I am content in the fact that many of the people I developed rose to be people developers themselves.

In fact, I had lunch with one such person on Monday and that is what prompted me to write this piece.

If you liked this or any of my past articles, please support my newsletter by subscribing today! Free or paid. Both are a huge motivation.

Follow me on Twitter @racheleesthinks if you are a startup diehard. If you can bear my periodic ranting and cursing, try me also @rachelees69.

Taming the Risk Beast

Simple Ways to Minimize Trouble

Personal Development Series

In The Risk Gene article, I went over some of my own opinions on how risk can lead us to dark places. It can make us expose ourselves to too much risk. We can wind up making poorly calculated decisions (e.g., risk outweighs reward). And, risk can also be, in and of itself, a thrill that people proactively pursue.

In this Part 2 article on risk, I would like to share some of the things I have done to tame my own risk beast.


Almost every successful risk taker mitigates risk. An investment firm will use several risk mitigation methods to protect itself. A personal investor will do the same thing.

The two most common methods for mitigating risk is to (a) limit risk through reduced exposure (e.g., diversification, stop/loss) and (b) transferring risk (e.g., insurance, partnerships). In a way, the leveraged buyout (aka private equity) is risk taking with some controls built-in.

Venture funds work the same way. People think of PE (high debt-to-equity investments), venture capital (startups), and hedge funds (non-traditional or complex assets) as these super high risk endeavors. I think the media has shaped that reputation.

In truth, investors that deploy this “pooled capital” are extremely cautious in terms of constructing and relying on advanced risk management techniques.

TIP 1: Build a floor. While risk taking looks up at the ceiling, risk mitigation looks at both ceiling and floor. Of the two, pay close attention to the floor. Make the floor defined through quantitative methods. For example, I will invest 3 percent of my money. Or, I will limit my trades (i.e., exposure) to no more than 10 per month.

Of course, avoiding risk is also a form of risk mitigation. So, too, is accepting risk. When accepting risk, you have to monitor it more closely and regularly than under normal circumstances.

For example, if your company has a data center with both public and private servers, you have to accept the risks of having a corporate networks vulnerable to intrusions and attacks. External penetration testing goes hand in hand with risk acceptance and thus becomes a mitigation tool. So, risk acceptance often involves spending additional money to protect the acceptance.


I have been known to take unnecessary risks. Over the years, I got into a habit of asking very close loved ones and lifelong friends (the smarter ones) to test me. Similar to the penetration tests for a network, my close circle of family and friends are my personal penetration test.

Their biggest objective is to evaluate just how badly I want the reward. They know that I should only take a risk when the rewards are exponentially higher than the risks. I run into this situation a lot when switching jobs.

Let’s say you’re making $240k salary with $80k bonus and stock. Along comes an incredibly promising startup. They offer you $180k salary with $40k bonus and stock options. After you calculate the gain/loss across a range of best case and worst case outcomes, things will still remain unclear.

So, this is when a trusted friend or mentor that really help. My friend forces me to list ALL the rewards and risks - even the ones that are not quantifiable.

Tip 2: We are sometimes very bad at judging our own risk profile. Ask a close, trusted family member, mentor, or friend to help you assess an important decision that involves risk. Give them a full list of every risk and reward - even the non quantifiable factors. They will help remove some of our own built-in biases.


I know myself well. I get tempted easily. It has gotten much better as I have gotten older. Experience sure does help. But, I still have that hidden little “gene” that talks to me.

So, I go out of my way not to put myself in a situation where I can get tempted. All investment proposals get routed to an assistant. I became almost addicted to saying “I’ll give it some thought” instead of committing to anything.

All sorts of excuses work partially but they are not effective. Risk takers act on emotion a lot. They are also magnets for other risk takers. Hang around some conservative and dull people. 

TIP 3: Do not run with other risk takers all the time. Your professional circle should not be monolithic. That is a great way to be blinded in terms of risks. You need a baseline before you are able to judge what is too risky vs. not. If you hang out with risk takers, that line separating high risk vs. low risk will always move closer to high risk. Meaning, your baseline is poorly calibrated.

If you are a poker pro, do not just hang out with other poker pros, day traders, bitcoin investors, and bungee jumping thrill seekers all the time. Balance your F&F circle.


I have this overall idea on risk that takes some explaining. Many people give me a quizzed look when I make this point.

It is not wise to take big risks when you feel you have “nothing to lose.” The phrase alone is a good sign that you are not in the proper mental place. Think of a janitor. Most people would agree that taking a job as a janitor is pretty bad - and hard.

How bad must things be for someone to become a janitor? People who feel they have “nothing to lose” would never take the janitor job. They would rather <<fill in the blank.>> But, this is a very dangerous way to think as you will invite in the worst kinds of irrational risk calculations into your life.

Remember all of this the next time you see a janitor. He or she is to be respected - not looked down upon. No one chooses to be a janitor. They are fighting hard to get out of a tough situation. They have “nothing to lose” but doing something about it to change the losing streak.

When you have nothing to lose, you need to go into a build or rebuild mode more and think like a turtle. Slow, gradual build mode. Not fast growth or shortcut mode.

Conversely, most people who think “I have so much to lose” should be more open to risk taking. First, you have accumulated enough in your life to be in a good situation. In the worst case, you can rebuild quicker if things go royally wrong. In the best case, you will be in an even better position while not having put it “all on the line.”

I bring this up because it is fairly common to run into young people or older folks suffering a major setback to think they have “nothing to lose” and swing for the fences. And, in my mind, this is exactly the opposite of what we should be doing when feeling cornered, desperate, or distraught.

If you liked this or any of my past articles, please support my newsletter by subscribing today! Free or paid. Both are a huge motivation.

Follow me on Twitter @racheleesthinks if you are a startup diehard. If you can bear my periodic ranting and cursing, try me also @rachelees69.

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