I have had plenty of time to grab at different parts of the elephant of success. At the same time, I find myself at a crossroads about which route leads to success.

What Does The Elephant Look like?

I have a rolodex of cautionary tales, which I will juxtapose with stories of my life and experiences. The tales before me combine reaching for the pinnacle of success with the fall that comes from over extension. I don’t think I have a picture of the entirety of success. I don’t know how to make it into a formula that I can use again and again. The topic is big. I liken it to being confronted with an elephant in the dark. My friends and colleagues make up this elephant of success, jeopardy and doom. I have put a lot of attention to grabbing at the elephant and trying to get a feel for it.

Cautionary Tales

One was a tireless worker. He would fix people in his laser like glare and convince them to get on board with whatever he was selling. I would watch him start a call with some who said, “I’m quitting” and end the call with getting their collaborator convinced to double down. He was able to bootstrap himself towards a $15-million deal. He rage quit that deal. He also worked himself to exhaustion and beyond. He was almost my age, but he drove himself to the point of organ failure. I went to his memorial a week or so back.

One was talented, personable and charismatic. He would go missing from time to time, so severely so that his clients would track me down for answers. After one of these disappearances, we spoke on the phone and I could not figure out why he sounded so different and muted. It was because this was the first time in two years that I heard him speak to me while sober. In every other interaction (and there were many) he was a little or a lot drunk. For a time, being drunk didn’t stop him from getting into a jet-setting lifestyle and earning over a quarter-million per year. That all came crashing down when his drinking got the better of him. He ended up losing it all, save his talent and his alcoholism. We worked together in a period where I was working half as much as him and earning about 10% of what he was able to bring in, He drank away all of this potential and prosperity.

One friend of mine booms and busts from wealth to poverty. One day he may be searching for coins in his couch to cover off the cost of a Starbucks. The next day, he’s ordering caviar in Venice. He gets some healthy six digit contracts. He does them and before the clients part from him with the delivered work, he will tell them all of the shortcomings of their plans and the project. He may even quit one project when a better project comes along. This tends to lead to a trail of wreckage of undone projects.

One guy who I used to work could never say, “no.” I worked with him on what could have been a cool project, building predictive algorithms for websites. I listened as he talked with a cardiac monitoring company over the phone. When he hung up the phone, he said, “we’re doing this for heart monitors, now.” A week prior, it was for a smart TV remote control and a month before that, it was to be a product for a gaming website. Everyone he talked to sold him on using our code for a variant idea. And everyone of those conversations resulted in work passed on to me to execute. He would include me on these calls and would lob responsibility over to me with the question / claim, “This shouldn’t be a problem should it?” It was a move to get me to either affirm his madness; or put up roadblocks and make it sound like we were amateurs. I would hold the party line then express my concerns afterwards (well, okay: I’d freak out to him). It was such a mess.

Then there’s my own capacity to be a cautionary tale. With 20+ years of web development under my belt, I want to be done. That means that concentration and passion are white knuckle exercises in fighting distraction and self-sabotage. I get credited with being a hard worker and an innovative fellow, but that needs to come in with a caveat of “when I care.” After this long in the game and so many years of anemic projects and deadbeat clients, I don’t care that often.

It’s time for me to go. But where?

I know what success looks like; it’s more than being busy. I know people who have “made it:” they go on long vacations; they work short work weeks; they spread their prosperity; they help others; they live long and they live large. A big part of success is building something enduring. My friends who burned out didn’t have that. The busier they got, the less enduring their ventures became until they ultimately broke down and their ventures disintegrated. If it’s time for me to go, what do I do? If I had one idea, it could be my way ahead, but I’ve got a few candidate ideas.

The Winning Horse

The Ground Rules

I look at people who succeed. For the cautionary tales I gather up, I also gather up stories of success and “hacks” to get somewhere. There are many and I there are online business rules I have learned:

Collaborate and Compete (sometimes)

I will collaborate and share notes with potential competitors. There are only so many good gigs out there, but there are many so-so projects that you can turn into a success; and lots of excellent projects that you can wreck through bad conduct. Rather than scrap and scrape for the one good project, I will throw a wide enough net to get the work I need. When have been I am going head-to-head with a competitor that I have a relationship with, I will usually say, “X is a good guy. I think you’d be better served working with them.” and once in a Blue Moon, I will go to my competitor / colleague and tell them that a client may want to go shopping. Sometimes they hand over the client; sometimes I help the colleague and they make their client happy. The energy lost in a competitive situation is energy you don’t get back. Likewise, squeezing a colleague doesn’t help someone you think well of. So: I tend to collaborate and will compete in the same space rather than compete for the same work.

Find a Fishing Hole

Facebook has a lot of the social media users, but not all of the social media users. Some people won’t touch the platform. Still: it’s wildly successful even with a partial market share. To succeed, one doesn’t need all of the market share, just enough to make the project viable. I’m always finding these new obscure businesses out there that make a killing. Find an audience or a market share that you can cater and then set up the delivery mechanism that matches the audience.

Right Size Your Net

I have said, “I need one dollar more than I could spend.” Is that a million dollars or a billion? Likely it’s closer to the former. To be considered successful, all I need is enough plus some padding without the income becoming painful to earn.

The formula for “enough” is simple. Extrapolate back from your ideal income. How much business is needed to yield the ideal profit? In one exercise, it looks like I can have a successful venture with 4000 paid users. Not Facebook’s 1.7 billion. I need to tap into 0.005% of the market share to be happy.

Ideas Are Cheap. Execution is Everything.

I have signed NDAs before I heard business ideas. When I considered getting involved, I hold to a “three strikes you’re out.” approach. Asked to sign an NDA before I hear an idea is a punter move and it earns a strike. Ideas are cheap. I bet I get 10 $1-million ideas a week. Who cares? The real work with any idea is execution. If someone needs me to sign an NDA before I hear their idea, I will listen; I may even work on the project; but I’m never going to steal it. If you want evidence that I think ideas are not enough? Keep reading: I’m going to dish out a bunch of ideas.

The Horse Race

I have ideas to proceed with. If I had a clone army, I would hand each of my clones one of these ideas and say, “go!” If I had a million dollars, I would divide it to launch at all of these ideas and see if one wins or if four of them all speed across the finish line.


Newspapers are dying. With their demise, goes the proud profession of newspaper carrier. At the same time, kids are becoming more and more comfortable with the same technology that’s killing the old world. There are lots of twentysomethings with great tech jobs. What if those kids could get their feet wet in their teens? Offshore developers charge $20-30/hr. for decent coding. A lot of kids would jump at the chance to make $20/hr. instead of $8/hr. flipping burgers. What if there was a way to get kids into the field of web development? Enter TeenPress (okay, the name is going to change). Parents would enroll their kids in an online learning certification program. The courses could be modular and a module could be capped off in a weekend or less. Kids could get the skills they need to enter into this lucrative field.

My first run of the math of this makes this a viable idea if we keep 4400 kids enrolled at any one time. There are 44,000,000 teens in America and another 50,000,000 in non-American countries where English is prevalent. I would need to pull in  0.005% of the market to make this viable. There is a diploma-mill with a penchant for purloining intellectual property, but I think their instructors wouldn’t be able to deliver and their students wouldn’t be able to succeed. Even if they did scoop the idea, all I need is 5,000 students and my concept will fly regardless of who else is in the marketplace.


This is possibly my most mature idea. For a couple years, I sunk A LOT of time into developing a management tool for housing co-ops. Things happened and my business partner is proceeding with the housing co-op software but I have the right to sell a variant: a condo management tool. I have dubbed it “Den.” There are hundreds of thousands of strata properties in North America. A client will fetch about $5,000-$10,000 per relationship lifetime. Ten clients would yield me an okay cash flow. A hundred clients would gross us something like a million. If we got up to 1% of the market share, the company would be dragging in a lot of cash.

Ebooks Galore

I came by a big database that can be sliced up, those slices curated, bundled and sold as ebooks. From the data I have at present, I could put together 100 ebooks. Best of all, this is a largely automated process with one human step to curate the elements; and one to do the finish work (cover, teaser, etc.). I have made contact with a marketer who will partner with me. The question: will these sell?

The Keto Affiliate

Try to find food to eat at the grocery store if you’re on a ketogenic diet. If you don’t want egg, dairy or meat there are few options in the grocery stores. There are a number of products for people on the ketogenic diet, the Atkins diet and the paleo diet– but they seem to be absent from store shelves, yet available online. My thinking: research the foods that work for me and post the results. If I like the product, I could offer an affiliate link to the product, popularize what I’m talking about and make more from affiliate revenue.

The Rebuild Coach

I had a really good orientation session with a coach who walks people through the process of becoming location independent. She heard about my story and about The Rebuild. She encouraged to start coaching people on rebuilding their lives. The problem(s): I am not a certified coach. Non-certified coaches freak me out. Second: I don’t know if anyone is eager to hear what I’m doing or what I have  discoveries. If it’s not popular, who would follow it? Third: I’m not done, so it feels like I don’t have evidence that it’s the right approach.

Do Nothing

The other horse in this race: doing nothing. Right now: that’s the winning horse. I am doing web development full time and wishing to evolve past that phase. With 21 years in the field, I am way overdue to grow and evolve. Five years ago, the property management service was my ticket out and that didn’t happen.

Which horse do I bet on? I could rule out the long shots and those that don’t fit my skillsets. But none of these ideas are coming in from left field. I have not planned to be become a lion tamer or a submarine captain. All of these ventures draw from what I know to do, what I’ve done, what I have ready at hand and/or a combination of these qualities.

What can I do with that lead horse? Some of these ideas are more than just interesting to me. A couple of these ideas could bring investor and partnership interest. My intention with these: put out a product or service that scales and get big enough to automate the project to the point where I not involved in the day-to-day. At the founder emeritus, I could get some of the proceeds, but leave most of the money for the people doing the day-to-day.

Maybe none of the horses need to lose. One person I’ve been following, Sol Orwell (https://www.youtube.com/watch?v=gJw5ARtrliA), starts ventures, hands them off to a manager and then launches the next idea. Maybe all of these horses can all yield results. My late friend was juggling six companies when he died. One cannot fight a war on two fronts and prevail. If I do want to let all of the horses win, which one gets across the finish line first?

What do you think? Is one idea good? Should I do them all in series? Do any of these interest you? Do you want to team up?