I’M PIVOTING! I’M PIVOTING!

Bob Wakefield
Data Driven Perspectives
7 min readJul 29, 2018

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Amy Hoy, whom I’ve never met in person but is absolutely delightful on Twitter, has turned into an unexpected source of inspiration for me. I read something by her where she talks about having a “fuck this shit” moment. I had mine back in June.

Growing up, all I wanted to do was fly the F-15. That dream went up in smoke pretty quickly after the Air Force changed the regs on asthma. No big deal. If the Air Force taught me anything, it’s to adapt and overcome. Over the years, this has turned into my person mantra.

So I figured, if the Air Force won’t let me fly their fancy jets, I’m just going to have to buy my own. I’ve been working on that goal since I was 19. I’m 41, and I’ve never been further away from my goals than I am right now. Fuck. This. Shit.

It’s pretty simple. Jet ownership isn’t cheap, but it is doable. You can pick up an L-39 for less than $100k. If you know the right people, it can be even cheaper. Problem is, every attempt I make at trying to generate large piles of cash usually starts with having to invest large piles of cash. Undergrad. Real Estate. Grad School. Hell, even Amway wasn’t cheap when I was only making $8/hr back in 1998. For the past 22 years, it’s been two steps forward and five steps back. With all of this work and sacrifice I’m putting in, I’ve ironically managed to basically ground myself by having so much cash wrapped up in debt service that there is none left over for avgas. I’m a human Kiwi!

Recent photo me.

In June of 2018, I had to admit to myself that I was bad at business. That’s a tough pill to swallow when you’ve got an MBA, but Wakefield’s first rule of problem-solving is to identify the problem, and I’ve never been one to tell myself comfortable lies. The problem was, I was doing “okay.” I haven’t had a job since 2006. I was generating revenue with my consulting firm, Mass Street Analytics, Inc. But all this money was obscuring the fact that I was massively phoning it in when it came to business development. I got mad. I pulled out my pen and literally went back to the drawing board.

Actual picture of the drawing board

It’s time to do things differently. High volatility in revenues has always been a challenge. They need to be smoothed out. It’s time to develop more than one income stream.

Step 1: Launch a series of courses on the Udemy platform.

This is stupid easy and I’m angry it took me so long to pull the trigger on this. I have MOUNTAINS of information between my ears. I don’t have time to write a book. Additionally, I’m constantly explaining the same thing to different people. Online classes just make sense.

I can’t just do a generic class. There are enough of those. Every class I do will have my special sauce slathered all over it. If I teach a class in Python, it’s going to be served up smothered in Bob’s approach to software engineering with a side of Wakefield’s 17 years of IT experience.

As of this writing, the first class is in the chute and expected to be published sometime in August.

Step 2: Get out from behind the computer

This isn’t difficult; I have just had zero motivation to do it. For years, I’ve sat back and watched as recruiter after recruiter brought me deals. It couldn’t have been any easier. I found a hole in that plan in 2017 when my phone stopped ringing. I can’t rely on others to bring me business. I need to generate it myself. I already run two meet-ups, so it’s not like I’m a total hermit, but I don’t run them with the explicit intention of generating leads. Bad business person. Bad.

I also need to do lame networking. I don’t mean be lame at networking, I mean networking is lame and has been since college. That being said, it is a basic and easy thing to do and I’ve been lucky enough to find a community of other business owners to tap into. I can start there and work my way up to going to formal events where I work the room with a glass of champagne in my hand and talk to people like Preston Uptight III and his wife Buffy about their weekend on their yacht. I’m taking it slow, here.

Step 3: Spin up a new firm

Already done. Kasold Software Inc. is a thing that exists. (Jayhawk fans will see what I did there.) Kasold is going to be a SaaS factory. We’re just going to churn out one business idea after another and take the approach that VCs do: make a bunch of investments and hope one hits large enough to cover the losses on the others.

This is key, actually. A problem with past ventures is that they take years to develop. It could be two to three years before I figured out something wasn’t going to work. Enough of that. Success can be a function of persistence if you get into a proper cycle of iterating over ideas with improvements after each evolution. It was clear that I needed more at bats. So instead of spending months on any one thing, I’m going to work on a bunch of stuff, stand up an MPV quickly, and determine viability. If it bombs, it bombs; I’ll open source it and move on.

The first SaaS product is in the pipe, but it’s in stealth mode. There isn’t even a landing page, yet. Coming soon. I have a multipage Word doc of ideas, so it’s not like I am lacking projects. Most importantly, I’m not doing the Wesley Snipes thing and betting it all on black.

Step 4: Start doing digital business right

I have a website. It sits there. I’ve applied no SEO to it whatsoever. That’s how pathetic and lazy I am. I really thought just having a website was good enough. It’s like it’s 2004 up in here.

I need to start doing the things that are expected of the web presence of a modern business like:

1. Having a blog.

2. Having an opt-in signup to follow said blog.

3. Have a landing page for special products.

4. Doing basic content marketing with warm emails.

5. S. E. O.

This is so basic. But necessity is the mother of something something, so if I didn’t have my personal ambition poking me with a cattle prod, I probably wouldn’t be doing these things.

Step 5: Find business partners

This is also key. I don’t want Kasold to be a software shop that builds things for other people. I want to build things WITH people. Instead of charging a fee for building something to spec, I’d rather partner with a business to implement their vision and carry some risk for a share of the revenue.

Business benefits:

1. Lowering their risk profile.

2. Lifetime support and expertise for the thing we built together.

Our benefits:

1. An endless stream of cool business ideas that we get to vet.

2. An ongoing revenue stream instead of a short hit of cash and then back out pounding the pavement again for new business.

The plans for this are still on the drawing board. Out of all the things I’m doing, this is the most exciting and I can’t wait to start spinning stuff up.

Step 6: Become a superhero

You think I’m joking. And old acquaintance who is a serial entrepreneur is spinning up a new firm and has decided to bring me along. I’ve had the chance to meet some of the other principals. They are putting together a team of Super Friends. No kidding. There might be capes.

This is also still incubating, so I can’t talk much about it. I’ll write more when I know more.

The goal here is that everything I do needs to somehow generate revenue. One thing needs to feed another until it becomes this self-aware organism whose sole purpose is to funnel cash to my bank account.

I’m not sure why it took so long to get here. The realization that my life is probably more than half over had a lot to do with it. Regardless, no more hiding in the trenches. Lock and load. It’s time to wreck shit up!

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Living at the intersection between finance, economics, and data science/engineering. Follow me on Twitter! @BobLovesData