Philosophy

Anatomy of a Death Spiral: the Inside Story of the Firesale of a 7 Figure Business

I recently sold my business – a business that I had for 7 years and concluded my involvement in it.

I sold out a longtime friend/client/ally for a fee that represents some of the value in the leads, contacts, processes that were working well, but we didn’t get the multiple that one would hope for after this time.

But that wasn’t his fault, that was mine.

Because I was actively working it, I wasn’t free to talk about things.  Hard to admit mistakes when clients can find the information.

The sale straddled 2018/2019 but the business really got away from me in about 2015. I made mistakes that made it into an inadvertent Ponzi scheme, and never recovered despite working hard.

The process of watching it slide sucked. There was very real grief involved.

I’ve wanted to have a reckoning of every major mistake that I made, or every factor. A medium-style post mortem on what went wrong.

Now that I’ve moved on, I am feel free to write this. There were many things in creating my company that I did right. But nobody needs any more self-congratulatory navel-gazing, and it’s more useful to talk about what I did wrong.

I Had Unsustainable Personal Habits.

I was really into the “rise and grind” vibe for a long time. I didn’t have a schedule that would allow for anything, and I wasted time in a variety of ways.

I was eating badly. I drank way too much to be healthy. I bought into the Valley myth of the Iconoclastic Asshole. How could I be wrong?

All of this was wholly independent of the stress that I was under. I became a caricature. I believed that I was Tony Soprano, or Walter White. One step away from doing everything right. I was more like Chris Christie or Donald Trump, delusional, angry.  Nuts

The truth was there was no time to reflect. Every moment was scheduled. I was hopping from crisis to crisis, and not storing value anywhere, not keeping up relationships.

What I’ll Do Different: I’ll maintain good habits personally, exercising, laying off the booze and I’ll make sure that work is in its box. I’ll work with more efficiency batching things and using a schedule to do what I’m supposed to do.

I Wasn’t 100% Sane. And I Isolated Myself.

Mental health is a thing. Not a lot of people talk about it.
And the pressure that I was creating was getting to me. I had thoughts that are perfectly insane. I know that I had them, I know that I believed them, but I have no idea from whence they came. The habits above interlocked with the insanity.

This manifested in what we’d say was disordered behavior. A lot of the good things we were doing were multiplied by zero because I’d take a testy remark and blow it out of proportion. Or I’d fire a designer that we didn’t wholly support.

I was creating and escalating conflicts just for its own sake.

At home, my relationship with my family was deteriorated and bananas My wife was under a ton of pressure as she was completing school. I was bitter about tuition bills, and I didn’t have the tools to address any of it correctly.

I was absent from being a kind companion, and I didn’t have first principles. Things were very bad, very bad, and we didn’t see a way away from any of it, so I largely ignored it during this time. I wasn’t really committed to being a family guy, I thought any sacrifice was worth it if I could…build some company and get some sort of business week cover or something.

What I’ll Do Differently:

Family first. Relationships first. Good, clear thinking. Easy on the booze.  Sleep / diet / exercise will all have rules that I’ll follow.

I Took On (WAY) Too Much Overhead

This was the key part of of the deterioration of our company. I knew – and know – I can sell. I felt like I needed to have some pressure on me to keep selling. I was always able to make it rain when necessary. Because I’d always sell to our expenses and spend too much time involved in delivery.

My wife is still mad about this. I went from a cheap place in the exurbs to a pricey place downtown. I went from a nut of $3600 a month in outside expenses to $15,000 a month. This created a different dynamic and a different need for cash that I didn’t have previously.

I hired people to staff up without paying attention to how well (or poorly) we were delivering our work.

What I’ll Do Differently: Profit First by Mike Michalowicz will run my life. We’ll pay off money as a first thing we do, not as a second or third.

I had No Hiring Process (Except My “Gut”)

I didn’t realize that we were in a brutally competitive talent market. That what we needed was a specialized skill. There were marketplaces for freelancers that were available to me. I am a Moneyball fan. The gist of that book is to work around warts that don’t matter, to hire for production and talent, not for potential.

But I had no rubric for warts that did matter.

I fancied myself an expert and I hired a ton of creative professionals who had warts. Some of them did matter. I had no real process in place, so I’d interview, buy lunch and make offers.

All of the “mishires” had clues. A process would have found them.

One creative director had left a trail of bodies that I would have noticed had I bothered with a little reference checking, or a deeper conversation about the story.

Another animator had never really done the work in his portfolio. Any process would have fixed this. And in many cases, I hired for affability, rather than other factors. People that need jobs get good at figuring out what you want to hear.

What I’ll do differently:

I’ll build a hiring process that is sustainable, and a general post-mortem process.

We Became A Ponzi Scheme

Because we had overhead, now we had to sell to fund it. That was fun. I got better at selling. That was also good and worked as intended, but downstream, it hurt.

I was able to close more deals for more dollars. We had a pricing scheme that offered multiple videos for cash now. The only KPI was dollars in. Not future liabilities.

We got no better at delivering, and created no processes (other than zeal) for delivering work.

All of this mean we had to hire suppliers, and fast. And as I said, I had no process. So they didn’t get “plugged in” to a system that works. A lot of our hires were poor fits. And they may have even been good fits for what we’re doing, but we didn’t have a good structure in place to organize it all.

So, what happened was that we became a Ponzi scheme. We needed new work to fulfill past orders. We then had sudden pressure on pricing that wasn’t the case when we began. We had been trapped by this.

I called this a “legacy issue.” I figured that sales would cure all, but when each sale may have been at a loss…well, it was harmful.

The lessons here:

  1. You have to pay labor costs even when work is utterly and absolutely unusable.
  2. Mishired employees generally don’t care about if the work is good or not, they want to be paid.
  3. You get the double whammy of refunding clients when the work is terrible.

What I’ll do differently:

We’ll measure the company in terms of what we can deliver, and who we can onboard and exactly when but not what we can sell.

We Took Factoring Loans

As a last ditch effort to make things work for us, we took on a Factoring loan. This loan would cover the refunds as well as some new staff to deliver work.

Don’t know what these are? Well, they are the loan of last resort for companies that have some cashflow. They charge insane markups over very short terms, but they aren’t like bank loans in that they don’t take forever to get.

Basically, we borrowed $35,000 and had to pay back $48,000 on an insane daily schedule (like $325 a day.) This was often repeated (called refactoring) at slightly better terms when there was pressure.

They were silent partners, and they were merciless. “Things aren’t working? F@#% you, Pay me.”

You delude yourself into believing that everything will work out, and I suspect that sometimes they can, but they are brutal tools, loans of truly last resort. It allowed me to kick our issues down the road. And it felt like relief when we were funded. But, the net to us was that we were in deep trouble, and we had this bandaid that also acted as a tourniquet.

We Left the Portland Community

25% of our business, and 30% of our contractors came from Portland agencies and the community. We could do some things to maintain the relationships that we had, but when it was clear I moved out of Portland, and that those relationships were farther, and that I wasn’t local (and there for the long hall) a big bit of business dried up.

I wasn’t able to get the benefits of being part of a community without contributing to the community. I underestimated the impact of this.

I moved – and the move was ultimately good for me- but it was in fact bad for the business.  I should have

We Took Our Cash-Cow to the Slaughterhouse

We got by because we sold a small part of our business to Telestream. That business was something a cash cow, paying us money over a long period of time without a lot of maintenance. This was a library of clip art that could have been the basis for a big business- we were early to the party, but we made an early version of the type of company that Videoblocks became.

We had both direct and channel sales, and it was staggering how cool that that was.

We were earning nearly five figures a month in sales and the work that we were doing wasn’t really costing more than a few hundred dollars each month on SaaS and hosting.

When things got a bit tight (and in order to pay my end of a buyout), I traded that in for a one-time payment that covered a few expenses and also had the impact of masking our problems.

What I’ll Do Differently: Nathan Barry of Convert Kit famously says that “all revenue isn’t created equally,” and any type of automated/recurring revenue is what I’m chasing.

Our Work Got Worse

In creative services, it’s ALL about the work. And honestly…how could the work get better in a situation like this? We were accelerating into some sort of chaotic failure spiral. We had a problem of being able to easily overwhelm our demand.

So, the work we delivered got worse.

Our reputation got worse.

My reputation got worse.

And I was insane, having this denial/high conflict style that wasn’t working at the time. My ego was out of hand because, after all, I built a seven figure business.

The net impact of “worse work” was that we had lost the rehires and referrals that drove our growth prior.

In the past we’d deliver good work. Almost always, that work would lead to more. Our clients were taking delivery of the work, but they weren’t getting the “Woah, who did THAT,” that we used to have (both during and after my former partner’s contributions). That created what was known as net promoter score and that built a nifty business.

A big reason for that was my former business partner’s contributions. He was a great dude. I bought him out because I wanted to create a different type of company, and because I worried about his burnout.

We would have needed to be fortunate in order to make this work.

What I Would Have Done Differently: I would have standards for the process and deliverables, and we would have enforced them at the best scale we knew how.

Sales Can’t Cure All If More Sales Makes the Problem Worse

The Factoring Loans killed us. Our daily payments denied us time to escape. That was a voluntary cancer that added too much to an already gravely wounded business. By the time we were out of the payments, our company was too much of a mess to be worth keeping.

More importantly, the impact of delivering bad work for a long time also wears on you. It erodes your confidence as a salesperson. It feels terrible, and it felt like I was not really helping anyone when I was selling.

It quickly got to the point where I knew the difference. I was no longer willing to access my network. That hurt sales. I couldn’t vouch for my own company. I was stuck selling to strangers and acquaintances, because I respected my network too much.

I knew I’d make a comeback at some point, and I’d need my network later. I kept thinking that I’d need ‘em in just a little while. That I’d get clear of the bad stuff and I’d be able to re-access them.

In retrospect, I’m glad I preserved the network I built and didn’t burn up too many relationships. It makes me trust myself more than I might have had I become cynical and tried harder to liquidate them.

What I’ll Do Differently:

I’ll focus on quality of the deliverables, quality of the business and margins. Doing work without margins isn’t fair to us.

How We Got Out Of Our Death-spiral.

We wound up having the soft-landing-to a sale. We spent a couple of years as a shabby company licking its wounds. To some extent I regret having not just crashed it into the rocks and let it go. That may have put me in a better place, than the long, slow decline. Or, when we were clear to staff it back up, but I lost confidence in delivering amazing work, but not the need to deliver amazing work.

To get out, I slowed down payments to providers (and yes, that hurt my relationships). That type of management was never a strength.

We also outsourced our work to a good-enough-for-us offshore team. We mostly got away with it and built a communication process around that. The margins we earned then paid the legacy costs. This allowed me to have a “soft landing” instead of a “brutal crash.” It wasn’t ideal, and there are good people that have good reasons to not like me very much.

Other Mistakes:

In no particular order:

  • Not automating anything: We left automation alone, arrogantly.
  • Not building a platform: This was a big mistake for us.
  • Not maintaining an email list: we were never consistent here and we never got great at it.
  • Not documenting enough things: A lot of our processes were one offs, and we never got in the habit of doing this right.
  • Not having a dashboard of true reality: We had no KPIs.
  • Not firing fast enough: We didn’t fire anyone.
  • Not pricing right:
  • Accepting unsuitable clients.

All of that stuff was, at various times, a big factor. I’d suspect that pricing was the biggest factor that I didn’t bold out, but it’s not a moral failure so I didn’t mention it.

What’s Next For Me?

I’m not sharing too much just yet.

When a dream dies, there’s some grief involved.

Processing this grief and thinking about this stuff took time. I underestimated that, and it took a while for me to be ready for whatever comes next and to put my shoulder to the wheel.  I had to heal.

I tried to create something that I wasn’t ready for yet, and it didn’t work because I hadn’t admitted and processed these lessons.  Now, it’s time to build the business I want. To use the skills that I’ve earned (the hard way) to make a company worth having for the long haul.

I’m trying to design a lifestyle-first business to support me and the team that joins me. I’ve got a promising horse to bet on. I believe in myself. I’m ready to reengage my network and to deliver good work again.

I don’t know if I’ll have the appetite to blog a ton, but I’ll be building and when cross the line from dabbling to commitment, I’ll engage here when I do.

Unfinished Business

I left Real Estate in 2008. In something of a huff, with the confident contempt that I’d never be back. Good riddance, we said to one another at the time.

I had done all the jobs in the industry, pretty much. The last one had me as a mortgage lender, and I was waiting out the time because we were planning on Ruby’s birth at the time, and the company I had had benefits. She was born, and I went into digital media for the past 10 years.

But I always felt that there was some unfinished business between Real Estate and I. An odd mix of revulsion and nostalgia. The “one that got away.”

The Substantial Downside

I fostered an honest contempt for many of the aspects of the industry. The NAR’s unseemly rent seeking behavior. The living caricatures that are Real Estate Agents.

The industry’s shameless, selfless studied and deliberate obtuseness that would make Upton Sinclair’s quote payoff:

“It is difficult to get a man to understand something, when his salary depends upon his not understanding it!”

Yes, the NAR is sometimes daft. But they do have confidence. And that goes a long way.

Then there’s the lifestyle aspect. By their own choice, Real Estate Agents are constantly “half working” zombies. The bottom line: they don’t generate enough business so they have to tolerate the insufferable. And that creates some type soul-crushing PTSD-eque kind of hollowed out vibe that they all share.

Them: always kind of working, but never really concentrating. A twitchy vibe where you feel like they are looking right through you. A lockstep but slow slide into human cliché always got to me. I did it, too. The erosion of integrity got to me. The industry in general is concerned with itself. Them’s the odds.

When you read the NAR’s code of Ethics, when you see what’s enforced at local boards, you learn that the majority of the work is an agreement to keep issues and problems in-house. Cooperation & Compensation. They brook no interference and they will get after you if…

“REALTORS® shall not knowingly or recklessly make false or misleading statements about other real estate professionals, their businesses, or their business practices. “

The brush, friends, is broad. Half the conversations I’ve here locally have been with Realtors just aghast at a top performing team’s advertising and how it highlights some of this stuff.

Then there’s the matter of Lawrence Yun, the economist who has all the credibility of Michael Cohen.

It was a daily battle to do right by and for my clients. The industry was either indifferent, or there were a coterie of self-aggrandizing ‘only honest’ agents. These were the ones that were midlevel producers, quietly shooting rocks at ther betters. Meanwhile, the board spends more clock time on “Realtor’s Duties to other Realtors,” than their duties to their public. Complaints and hearings centered around entering errant data into the MLS, advertising violations and procuring cause. Never would the public have pull.

The bottom line: Real Estate Agents generally make their own work. And they spend an outsized portion of their energy tut-tut-tutting the inferior ethics of their competition, or something. It’s a strange world.

The Significant Upside

And yet.

I say all this and I still want in. Selling houses is the biggest game in town when it comes to consumer marketing.

I’ve always identified with sellers. And I’ve felt like the purest form of the art was selling houses, stocks or cars. I’ve done stocks (albeit in a fairly limited way). These things represent the big American Dreams, ingrained in our culture from the Hamilton to the Homestead Act to the Capra Oevure to the GI Bill and more. Under all is the land, yano? And land ownership made America America.

I did well (if inconsistently in terms of effort and production) during my time as an agent, and there’s always been a tug towards the industry…a nostalgia.

When we were young and innocent…

There’s a low cost of service and you can make a significant impact at a key time in someone’s life. Most practitioners of anything are average or below, so by being great, you help the world.

You can also do it better and when you do it better, you can reap the rewards.

The income is good, the schedule flexible is good, the job is simple, helping buyers and sellers make good decisions is a good thing to do.

The Boundaries.

To start and to protect myself against the downside I’ll have to set up some boundaries. There are parts of any business I don’t love. And that’s normal, predictable, and part of the gig. But to protect myself from the bad parts of this one I’ll be deliberate about boundaries.

So I’ll go back. With the stuff that I learned at Simplifilm about delivery, production and client service.

After a 6 week “startup time.” I’ll cap my total hours at 35/week. This is enough. I’ll be around to make dinner, I’ll be around and present for my kids. Realtors spend time on drama, there’s an addiction to the potential use of time that makes them half-work all the time. I have to inoculate myself against that unfortunate trap

  1. I won’t feel scarcity and have to “always be selling.” I will talk about stories of families, but I won’t be in “realtor” mode when at family gatherings. I’m always appalled by the too eager-to-talk-real estate types.
  2. I’ll get in the best shape of my life during this journey. Can’t be a cliché. Gotta eat right.
  3. I’ll be available to my kids daily. I’ll be around to support their endeavors both artistically and academically. I’ll will do more than my share of the housework, and I’ll put my best energy into building a family structure and keeping our family organized and on point.
  4. I’ll continue to have a curriculum for personal growth and I’ll develop and continue to develop a life practice.
  5. I’ll leave energy for writing and for my own consultancy. I’ll work some type of split schedule there.
  6. There will be some rules around this, a series of Maxims that I’ll live by, operate by and use.
  7. I’ll spend a weekend each month away out of town and away from Real Estate. I’ll have some vacation scheduled each quarter.

There may be other things that I need to do – like having a second phone that goes away, or other similar things to help enforce boundaries. I’ll need to manage the expectations of my children. I set it up so that they are fairly self-sustaining in the morning. My wife is the best person ever and can’t be any easier to get along with.

The Plan For Production

I did some of my usual spreadsheets to figure this out and tinker with it. It requires diligent execution. It requires 35 hours of focus each week. To earn a robust and happy living, I don’t really need to have a LOT of leads, views or anything, but I need a few deep connections and people that “get” me. My actual tribe.

I’d say that 150 views over 6-8 months in a local area is REALLY good, and say, 500 subscribers is top end (for this business). I’d want to have a list of say 3500+/- in a CRM where I was actively promoting things and sharing expertise. Once the CRM has “enough” names, we’ll have enough to market and remarket to.

  1. I’ll roll with this from a media first perspective. On camera every day. I’ll do this job from a media first perspective so that I’m recording and demonstrating expertise.
  2. Leveraged lead gen is key here. I have to use FB/Insta to make this work and have media that I can reuse down the chain.
    • Cost per lead needs to be ~$250 or so. A lead isn’t just a ‘meh’ inquiry.
    • I’ll focus on High Hanging Fruit, instead of the Zillow/Realtor.Com crap that everyone’s fighting for. Long-term relationships.
  3. I’ll do this with an operating plan. My income should gross about $420k/year and to net about $300k/year. This is just over $30k a month, or 3.7 homes sold monthly in the part of this market I want to be in.
    • (Object here is 45 homes per year, average price $355k, average commission ~2.65% or ~$9407.)
      • Object is to do 40% listings / 60% buyers first year. The 25 buyers will take 25 hours to deliver per buyer with good systems. ~625 per hour.
      • 44 homes a year:
        • Q1: 6 homes.
        • Q2: 12
        • Q3: 13
        • Q4: 12
      • “Wasted” buyers will be ~300 hours year. I.e. buyers that fall out. I’ll measure this and be gracious about it without feeling anything. The measurement will test my skills/assumptions.
      • 60 hour cap on buyer hours.
      • 17 Listings will take 17 hours to deliver per listing = 289 hours.
      • Object is to be at or around 15% to acquire business (ad spend + video production). $4500 initial investment and a “kitty” based on income.
      • 15% to provide services to them (pictures, gas, gifts, ads, vendors, brokerage services)
      • No substantial admin/assistant. Gotta do my own paperwork and rely on good title companies. Build a process using our tools.
      • This (ultimately) will be split 20 hours with or serving clients / 15 in lead gen. When I don’t have clients…I’ll spend the time on active lead gen.

Skills & Inputs Needed

Lead Sources:

First, I’m going to use the Platform system. We had a rocky start, but I like the ethos that they are striving for. I get that it’s aspirational and there’s a very wide gap between where they are and what they say. All visionary companies have one.

This will have me running some Facebook ads and building out landing pages to work with them.

Expertise

I’ll have to acquire some skill I don’t have. A quick list:

  • Market knowledge. To be gained by doing the neighborhood preview videos and a disciplined MLS study and export. This will include pricing and local preferences.
  • Paperwork Knowledge & Fluency I’ll have to get fluent again with the paperwork and disclosures needed. I’ll be doing those quickly and as efficiently as possible.
  • Listing Presentation I’ll do a listing presentation that’s about them and their goals. A lot of the listing presentations are bad. I’ll base this on The Perfect Webinar
  • Buyer Brokering This is the part that’s fun, and we’ll have to work with this in a congruent way.
  • Pricing I’ll look at as many homes as possible, and I’ll look to price homes appropriately and as professionally as possible.
  • Diplomacy Most agents are high-strung nitwits. In order for this to work I’ll have to suffer fools more wisely than I do today. I have an aversion to dealing with the “type” of poor communicator that fills the rank and files at your local brokerage.

First Projects:

To get this rolling we’ll need to have some projects done. None of these should take much longer than a day or so to build out, if I don’t dawdle.

  1. Create a branding and content calendar.
  2. Create standards for each video and blog post, and a way to assemble them quickly.
  3. Create landing pages.
  4. Create all advertisements that I mean to use & follow up sequences.
  5. Create a Listing Presentation.
  6. Create Buyer’s Presentation.
  7. Create a place for iterated processes that may be changed. (Maybe WorkFlowy)

So enough talking. 1900 words of it. Time to get this done in the context of the Life of Rigor that I want.

There’s unfinished business here. I mean to settle up.

Practitioner

One of the things I love about the current economy is its opportunity. People can be anything, do anything.

The thing I hate?

There are so many people that achieve a tiny modicum of success, they are one chapter ahead in the book, and they then stop practicing. They start teaching.

A couple exceptions would be my friend Liam and Anthony. These two actually have a growing sales practice in addition to everything else that’s going on with them.

The resistance to becoming a consultant was that I largely lost interest in Simplifilm, the “biggest” thing I ever did. I let it decay, I made some mistakes that chased me off the perch. I earned some bad reviews from employees, and I felt bad – like a fraud – even amidst the long-planned launch of a sales consultancy.

But I’ve gotta be a practitioner in order for me to feel like I have credibility. I gotta be real. I’m not going to be Tom Ferry or Alex Chafren, some amoral low-rent charlatan who never did, and never could do what he teaches others. The advice business is filled with them and I can’t do that.

I respect the people that do it too, the sergeants who “lead from the field,” a lot more than the people that haven’t. I’m not saying the information is inherently bad, I’m saying that I’m biased to respect the people that actually put their advice in the field. So I will.

Slash

Not too long ago, my friend Tim Paige was musing on Facebook about people with dual careers.

Dual Careers by choice, and not because they were beginners.

Tim comes from over in Voice Over, and there are a lot of people that do that gig part time. Or they do it while also pursuing something else. This ruffles feathers because the established providers in an industry never take kindly to tourists who threaten their income.

But everyone has to start somewhere. Tim was a VO/Marketer for a long time. Now he’s focused more on VO than other opportunities. I hired him as a VO during the time he was splitting time, and he was more professional than very nearly about anyone (and we’ve hired probably 250 VOs).

But I’ve always resisted doing two things. I’ve tried to focus on one thing because that’s what all the good books tell us. I was afraid to be the “master of none.”

Let’s be honest. I was afraid to be perceived as the master of none. I didn’t want to be one of those boofy haired weirdos that, you know, had some home-based candle business, does “social media”, worked in a Kinko’s and would be happy to sell you real estate.

Hacks. I recoil at the thought of being that guy. Being in sales has enough of that doubt as part of the game, but why invite it?

Then that post led me to consider the people I deeply admire1 and their pursuits.

Lauryn Hill: Rapper / Singer / Actress

Steve Jobs: Pixar / Apple

Ben Franklin: Politics / Lightning / Recliners

Winston Churchill: Writer / Prime Minister

Elon Musk Tesla / SpaceX / Pot Smoking

Donald Glover Director / Writer / Actor/ Rapper

Brian May Guitar / Astrophysics

There are others, obviously, even peers of mine that do a little of everything.

These are careers I want. Man! Like if the ONLY thing that Ben Franklin ever did was to collaborate with Jefferson and edit the Declaration of Independence, he would have been remembered today.

I’ve resisted having a slash career, and instead, I’ve sat in this paralyzed tail chasing circle. Because you have to commit, right? If you’re not doing just ONE thing, you’re not committed, right?

That’s what I told myself for a long time.

Because of ego, really. And because the flawed Startup Founder Hypothesis2 infected my thinking to my detrement. I was in a decision mode regarding building a business that can support the goals of me/my family. I spent a lot longer there than I needed to, because I felt it had to be very binary. One thing or another.

So I think I’ll have a framework to pursue this:

  1. Roles: These are things that we do with professional aplomb and esprit de corps. Liam Veitch does a good job with this in his roles at his agency and with Freelance lift.A role is a thing that we do for an open ended period of time that we mean to use to make money. There can be overlap with other roles, and they generally require constant efforts.

    I think that one can have, say, 2 main roles at a time. There may be exceptions if you’ve been in a business for a long time or one is largely passive (like a real estate investor or a board seat).

  2. Projects/Campaigns: These are things that (generally) have a finite start or end date. They take a lot of time, but there’s an end in sight for them. Examples might be a book project, or a website launch, or even an initial round of funds raised.The finite nature of these things them from being a constant mouth to feed, and keeps the “load” manageable.
  3. Hobbies: These are things that could pan out financially. A thing that you do in your 20% time, maybe. A speculative app, or adapting an internal tool for broader use. For me it might just be playing Poker.Apple famously has their iPhone, Macs as “main gigs” but they have the Watch and the TV as hobbies. Facebook has Occulus. Danica Patrick has her vineyard, and a consortium of entrepreneurs all bought an old mining town.

Excellence is table stakes when you have the audacity to be a little bit different. To pursue a “slash” career, you have to be great at everything you do and outperform your peers the lifers and other pseudohustlers. Because that will immunize your ego against the snarky voices that say that say “ah, this a part time gig for you?”

Hustle as Performance Art.

(Really cool poster by Joey Roth)

Most people don’t hustle. Sturgeon’s Law and all that. The big blue ocean is too big and scary for them, and they seek the familiar. I’ve been that guy way way more than I’d like to admit.

Like me, most people think they hustle. It’s comforting to think that we’re in the top 1% of hustlers. Whatever that means. It’s nice to believe that we are working effectively on our own hustle.

But it’s mostly not true. We’ve bought into the myth of “hustle” as performance art.

Here are the main ways it happens:

Fake Hustle: Some of us fake the hustle, posting inspirational quotes from Elon Musk or Steve Jobs or Walt Disney or someone else like that. They have to talk about every. Little. Thing. They. Do. As if that’s going making progress.

Grinders Still more “grind”. They do a ton of activity and a lot of effort. Little in the way of results. This is folks that do things in a way that’s always been done. The wear themselves out doing things that have no impact. It’s hard work but it’s not the correct work that actually matters. A salesperson that writes long and elabroate blog posts but never chooses to prospect. These are the people that eat SnackWells and spend hours on the elliptical trainer but never understand why they can’t use weight.

Victims Joey Roth’s classic image calls ‘em martyrs, but I like to call ‘em victims. These people are folks that “work so hard but nobody appreciates them.” We all are wont to believe that we, alone, are noble. That our profession has required a ton of sacrifice and dedication, and nobody appreciates us. That we’ve given up some more lucrative career easily available to us.

The Expert Burnouts There’s a class of people who have been in the industry a long time. Limited success. These folks can talk a good game, and “know” the industry, but the best fruits of their professions passed them by. But they are always waiting to give unsolicited advice to people entering the industry. They know better. And sometimes, they are right.

The Logo Collectors These are people that once did some project tangentially associated with a big prestigious brand, or person. They are too good for wherever they find themselves now because it doesn’t compare to their past glory. They give a limited effort because they are “above” this one, or it won’t work at this “small” scale. But they always talk about their past glories and spend a lot of energy ensuring we know that they once worked for Nike.

All of it’s performance art. We’re interested in appearing like we are hustling to relieve us of the obligation to our talent and the obligation to doing the hard work that’s needed to sail into the great unknown.

Notes On Hamilton

While Heather and I were driving around the PNW for a really great little 5-day vacation, we listened to Hamilton a few times.

I have been listening to the choruses for a long time, but I never had the chance to REALLY listen.

But man, oh man! This work was genius.

The density of the raps, the attention to detail (like the 9-year-old child was a really simple rapper.). The digs, jokes, and the fact that it was all polished.

There were callbacks and allusions to Grandmaster Flash, Eminem, Mob Depp and a lot more I’m sure I missed since I’m only a casual hip-hop fan.

I was left with a rare feeling that I was engaging a mind an order of magnitude more powerful than mine. Generally, Dunning-Krueger protects me from this, but not today.

Hats off to Lin Manuel Miranda. Belatedly.

To Be In Practice

One of the things about opening up a business is that you need to find your way to what you want to do.

In my case, I’ve missed out on being a practitioner of sales for a few years. Thinking back, it’s been over three years since I’ve really sold with the idea that maximizing revenue and numbers is a good thing.

That has put me in an “out of practice” situation. Add that to the fact that the sales industry changes itself completely every half-decade and I feel somehow “out of shape” in a way that I don’t think I have ever been. So I’m taking steps to change that.

Our biggest problem at Simplifilm was getting jobs out the door. Sales doesn’t cure all in that situation.

I’ve felt that way lately. In the advisory business, I’m at a remove from direct contact with my clients and my customer’s clients. That’s fine to a point, but there’s something appealing about being a practitioner. It’s the director who still acts as DP on set. You respect that guy.

Being a practitioner is appealing because it brings me back to an authentic place. To get punched in the mouth again, to learn what works right now. To connect.

For me to have gotten away from it for as long as I have was an error. Day by day it was defensible, but over the long haul, not as much.

So I’ll get back into practice in the next few weeks.

The setup I’m going to go for:

  • A business where I spend my time selling and marketing.
  • An advisory /consultancy that’s on the side.

This will mean that I may take the rest of the year to build the former up so I can turn my attention to the latter. I’m OK with that.

Dear Microsoft:

Dear Microsoft:

Listen, I am rooting for you. I love me a good comeback story, and it seems that you are dialed in right now.

And I’m glad.

But, look, you’ve got to respect me a little bit more.

I have two of your products: Office 360 and Xbox One.

And they both annoy me in exactly the same way.

I don’t play the Xbox one very often at all. I use Office360 as infrequently as possible.

When I open either, they both want to update. I don’t need the latest version.

I need to use the software.

I remember last year when I bought my Xbox. I couldn’t play Forza for like 6 hours because it needed a system update of some sort. Then it had to download Forza. This was after I signed in and jumped through all of your hoops.

I opened my Xbox the other day to play Rayman with my kids. I was logged out because I had to change my password.

Before I could log back in I was required to grab a giant update. No games would play. All of my downloaded games required a new update, probably the Xbox360 emulator or something.

What a drag, man.

So I let it do its thing in the background.

Whenever I open Microsoft Word, I know that it’s gonna want to update and bounce the dock. It’ll interrupt me and ask to close. It’s fine that you want to update, just do it in the background. I gave you permission to check automatically.

Here’s what I want:

  1. Don’t punish me for using your software occasionally. Let me work for a while and then ask to update tonight, tomorrow, in an hour. I get that you need to.
  2. If you MUST update (say once a quarter, max) for real reasons, do that behind my back. Make it so it’s hard not to bypass that.
  3. When I buy a product, no barriers to using it. I was a first time Xbox person, just wanted to race cars with my kids. Hooked up the Xbox at 6pm on a Friday night, and it took 4 hours to let me in is bogus. Respect my money. Let me play, then update. Who wants to wait to use something?
  4. Update in the background, like Chrome does. I think Chrome sets the bar for updating, doing it, seemingly while the software is running. Be like them.
  5. During updates on a Mac inherit the devices norms. Don’t bounce the dock, and make a show out of it. Just do your thing and be done. Go through the App store if you can.

That’s it. You have other issues (your Xbox One UX seems to inherit the worst mistakes of Windows 7 and an iPod Classic). But this one? This respect thing?

Well, it’s got me concerned. Maybe it doesn’t matter and we all just accept that 20% of the experience will be antagonistic. I’m not likely to get Office 360 again. I won’t if i can help it. I know that when Red Dead Redemption II comes out that I will need to plan on having it update for 4 hours before I can play.  So I’ll be annoyed at you between now and then for the time you’re planning on wasting.

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