Optimization, Automation, and Outsourcing

How to Teach a Machine Learning Algorithm to Identify Your Customers

I conducted some crazy experiments in my twenties; hacking the most effective strategies for using time efficiently. These methods have grown up, stood the test of time and became the OAO Methodology I use in my company, Less Doing. The process works across every imaginable industry and in all stages of growth, but we don’t just focus on the “growth hacks” or quite honestly any framework for actively seeking growth.

We look for the constraints, the bottlenecks, the hurdles that are stopping good ideas from naturally evolving into successful and prolific organizations.

The challenge with a system that works for lots of different organizations in very different situations is that it makes it exceedingly difficult to identify your customer avatar. I work with consultants, doctors, consumer packaged goods companies, government agencies. When someone asks me who my ideal customer is, I have to quickly try and change the subject because I can’t actually answer them.

So I had a theory, what if I could show a machine learning algorithm a bunch of my current clients and it could create a model based on them to compare against any new potential lead? Would the machine be able to “pick a winner” in a way that I never could?

Spoiler Alert: It can, and it does it with 93% accuracy

Now whenever we get a new person’s email address, whether it’s during one of my speaking engagements or someone simply opt-in to our newsletter (like you can do in the box below…smooth right?)https://upscri.be/6892b4?as_embed=true

The email is enriched with a ton of publicly available data, compared against the model, and if it predicts you’ll be a good fit for one of our program, I get a Slack message like this:

At that point, I can look into their company a little, and then craft a very personal message to open a conversation. There’s nothing underhanded or secretive about this, we are simply cutting through the news for both parties. I don’t have to send general, unhelpful content to everyone, and the person on the other end who could genuinely benefit from working with us doesn’t have to wait forty-five days to navigate an email autoresponder sequence.

Would you like to build one for your business? I can show you, just sign up for my eternal continuity program for 20% of your current salary by clicking HERE


I’m sorry I couldn’t help myself, I’ll show you the whole thing step-by-step right here, right now:

Step 1 — Get your customer data

You probably have a list of your customers somewhere, people who have actually paid you money for something. It might be in your email system (Convertkit, Mailchimp, etc…) or in your payment process (ACH, Stripe, Recurly, etc…) or maybe you have them written in a ledger in your desk drawer, doesn’t matter to me as long as you have at least ten of them. You want a list that includes as equal of a number as possible of customers and non-customers. You can just grab random ones from your newsletter for the latter group.

Step 2 — Enrich the data

I like a tool called ClearBit which can “enrich” your emails with up to 85 points of publicly available data like location, company name and size, seniority, Twitter bio, LinkedIn company description, etc…you upload your file of emails and it will return one with all the data added to it.

And we end up with a CSV that looks like this:

Step 3 — Teach the Machine

Now go to MonkeyLearn (use coupon code lessdoing for 50% off your first three months), create a new classifier, and upload the csv. It will let you choose which of the data points you want to look it. That part is up to you depending on whats most relevant to what you’re looking for. Location is probably not relevant unless you serve specific markets. Twitter followers might be relevant if you work with influencers. Seniority could be important if you need to deal with decision makers. I chose the most subjective ones I could think of, personal bio, company description, industry code. Then it’s just a matter of telling it which ones are customers and which ones aren’t.

Step 4 — Build the automation

Now that we built the classifier it’s time to do something with it. So we’re going to create a Zap using Zapier that takes any new signup to our newsletter, enriches the data with Clearbit, shows it to MonkeyLearn to tag it as a customer or not, and then if it is a customer, we need to be notified somehow.

For the classification text, you’ll have to choose whichever data points you decided to build the model based on. So at the point the image above finishes, Clearbit has pulled in all the info on the persons email but you need to tell MonkeyLearn just to look at the relevant data points.

I chose to get notified with a Slack message but you could make it and email, a text message, a Trello card, whatever works best for you.

Step 5 — Transfer Feelings

Extra Credit:

  • Create an additional set of automations to continue to improve the model by comparing the models prediction against what actually ended up happening
  • Automate the outreach to the person identified as a good prospect

If your business isn’t duct taped together, you’re doing it wrong.

Most of our time at Less Doing is spent coaching business owners on how to make their workflows & processes more structured, organized & efficient.

It’s a bit of a shock sometimes then, when I tell coaching clients one of our central tenets: “If your business process doesn’t sometimes look like a duct-taped structure falling apart at the seams, you’re doing it wrong”

A common thought exercise I do is ask people, if you had the choice between having a Rube Goldberg machine run your organization or a giant box with an on-off switch, which one would you pick?

The vast majority of people pick the latter, and it’s absolutely wrong.

One of the biggest things we learned when we were just starting out is that the best way to build a scalable, automated business organization is to break it up into pieces. An early mistake we made was investing thousands of dollars into an “all-in-one CRM” — it ended up being completely useless to us and continues to sit there gathering dust.

A smart, automated business has multiple moving parts which specialize in different business functions in your organization. Not only does this allow you to handle each business unit well, it also makes debugging easier — you have multiple points of failure that you can dive into rather than a single, massive, messy monolith.

For example, one of the companies we work with, ContentFly, has 73 different zaps running their entire platform AND company. 73! They have more zaps than they have lines of code.

People underestimate the sheer amount of powerful tools that are available, all flawlessly efficient.

Slack and Zapier is where it all begins — Slack should be the command centre of your operation, with Zapier being the pipes that bring all the other services in, allowing you to manage/monitor it from one place.

After that, it’s entirely up to you. Airtable is our weapon of choice, and Typeform is a great way of creating front-end or lead-in interfaces. Stripe & PayPal can handle your payments, while MailChimp and Intercom can automate customer marketing & communication.

If you aren’t using all of these touchpoints, in favor of just one catch-all system, you’re missing out on so much value. Each of these tools does their own specialization in a way that no catch-all will ever accomplish.

All told, we haven’t even brought up the best part of this: synergy.

By enabling multiple touchpoints, you can actually enhance the capabilities of each individual one. Zapier, for instance, has several Built-in Apps that let you format, filter & transform data before moving them from service to service.

You can literally automate everything.

Why give up that incredible power just to get hamstrung to a single tool? It’s an age-old mindset and a lazy one — if you aren’t aggressively fine tuning your processes and building a machine that can scale, you’re planning your own obsolescence.

Go build your Frankenstein.

But make sure it integrates with Zapier.

Stop Raging. Start Documenting

Access without information and instruction is painful, and totally unproductive. But if you document the process, the problem disappears.

I travel a lot, and I’ve noticed something pretty interesting over the years: hotel reviews are almost never accurate. Very often when I’m looking up a hotel to stay in, I find myself a bit nervous after reading the reviews — the shower is slow, the lobby smells, the security guy makes weird noises, the cutlery is dirty.

And every single time those fears turn out to be unwarranted.

You see, one of the unfortunate byproducts of the information age (and the internet), is that we’ve commoditized (and militarized) an age old human tradition: whining. To complain is a very human thing to do — unfortunately, the internet has allowed what would otherwise be fleeting methods of vented frustration to be immortalized.

The same exists for software — scroll through G2Crowd for any piece of software you use, and you’ll find a shocking number of people for whom it was an absolutely abhorrent experience. Tools which form the backbone of your work and productivity, others found completely useless.

How exactly does this split happen? It’s a problem I like to call access without information.

If you really think about it, the amount of tools we use on a day to day basis is astounding. With the boom of SaaS apps in the last half a decade, every professional has their own toolkit. At Less Doing, our big two are Trello and Airtable.

The issue is, there’s very little onboarding on these tools. Imagine being a blacksmith and you just start hammering away on your first day — you’d probably leave a bad review for that hammer on G2crowd too, wouldn’t you?

Because the cloud has made software so simple to access, the typical onboarding & training you see with enterprise software doesn’t exist anymore. So pretty often, new employees for example might jump into a tool and start using it in completely the wrong way, leading to bad process and a poor experience.

The funny thing about this is it’s easily fixable. There’s usually one or two simple adjustments that make the difference between a bad experience and lifelong software loyalty.

I’ll give you an example. I was reading in a Google Groups thread a while ago of a guy who was complaining that Gmail doesn’t have a way of keeping evergreen content — that it was easy to lose important information. He was requesting a “pinned emails” feature, where you could denote extra important emails and have quick access to them whenever.

If you haven’t caught on yet, Gmail already has this feature — starred emails.

You see, the guy was using starred emails sort of like a to-do list — in the morning he would star the most important emails in his inbox, and throughout the day he’d prioritize those over everything else. While it was a pretty useful way to use the stars, it wasn’t the best way, and as a result he was missing out on the most important use case of that feature.

This is a classic example of access without information.

In the workplace, this can cause a lot of process disruption and make the onboarding process for new employees particularly challenging. I’ve got two solutions I’ve found that work well: talk in assets absolutes and people absolutes.

When you’re documenting a process for instance, don’t speak on assets in relative terms — i.e, don’t say “for the next step, refer to the payroll document”. You’ve immediately added a layer of complexity for the individual… where’s the payroll document? Do I need a password? What tool do I use to get there?

Similarly, referring to people in an absolute sense is essential in process documentation. Never say “once you’ve finished this up, send it to Geoff at Accounting” — say something more along the lines of “send it over to the claims department in accounting”.

You see every time you speak in relative terms, you add another complexity point, which is often met by resistance. While a good employee might ask about it to clear it up, often they’ll just power forward and try to figure it out themselves.

Every time this happens, it builds up “complexity debt” — and complexity debt is the biggest problem with access without information.

So, simple lessons: asset absolutes and people absolutes, and be cognizant of complexity debt. And on the employee’s side?

Ask questions.

I guarantee that you won’t just solve your own problem, you’ll be solving the same problem for a lot of your co-workers who were too embarrassed to ask.

15 Tech Tools You Need Today

I do this private, live video every other week for folks in our Less Doing Academy, where I dive into the latest and greatest tech tools out there.

While I am most definitely “tool agnostic” in that I don’t worship at the altar of a particular platform or tool or app, sometimes innovations come down the pipe that just blow me sideways.

Now, I obviously can’t tell you ALL the stuff I found in my searches last week, but here are fifteen, you’re gonna wish you had developed, but are still thrilled they exist.

I am.

Happy Clicking!

  1. The new version of Gmail web.
  2. MasterClass for iOS — Learn anywhere from the best in the world.
  3. Create a high performing team culture right from Slack.
  4. A smart speaker with Alexa for kids.
  5. Order anything, right from Slack.
  6. Extract data from incoming emails and automate your workflow.
  7. Convert incoming customer texts into Intercom conversation.
  8. Schedule Instagram Stories from your web browser — FREE Beta.
  9. YouTubers, track progress towards 💰monetization & beyond 🚀.
  10. Simplest way to write and publish beautiful docs.
  11. The ultimate sleep cycle app for Apple Watch.
  12. Quickly find the perfect gift!
  13. Simple, collaborative checklists. Not powered by AI.
  14. Improve Your Decision Making Skills.
  15. Organize your research and notes beautifully ✨

The Right Way To Outsource Everything

The benefits of strategic outsourcing are no secret, whether implemented for personal or professional use.

It’s also no secret that I love outsourcing. After all, it is one of Less Doing’s three tenets.

But in the Less Doing mantra of “Optimize, Automate, Outsource” pay close attention to where the term outsource appears:

Optimize → Automate → Outsource

People habitually approach outsourcing the wrong way; they see outsourcing as the first step rather than the last.

Don’t just head to Fiverr and start outsourcing on a whim.

Identify the underlying issues of your efficiency problem — see if there’s a way to optimize the existing process or automate it via mechanization (software) — before jumping to outsourcing.

If you can clearly outline the reasons for outsourcing (and assuming optimization and automation are not feasible solutions) you can proceed with your efforts.

Of course there are those who would never even consider outsourcing as a feasible solution for any task.

My question to these people is simply, why?

The criticisms of outsourcing are — by and large — misguided.

Here are some of the most common objections I encounter from clients:

  1. I Don’t Know What To Outsource

Honestly, examine your last hour of work. There are probably three to five things we can potentially outsource. Don’t believe me? — Contact us.

2. How Do I Know They Won’t Mess It Up?

Well…you don’t. But how do you know you won’t make a mistake either? More importantly, how do you know that it can’t be done better?

3. It Will Take Longer To Explain Than To Do

This argument is actually somewhat fair.

Certainly during the beginning stages of an outsourcing campaign it may feel like the time spent to teach others how to perform the task outweighs the time required to complete the task itself. First, the process is a terrific way to hone your ability to give direction clearly. Second, once the outsourcing is firmly in-place your productivity should sky-rocket on the remaining non-outsourced tasks.

4. It Only Takes a Minute

So this argument is similar to #3 but I still feel it deserves its own place on this list.

A given task may only take sixty seconds to complete, but that single minute of distraction from core work creates a thought-flow gap. Most people need 20 minutes to recover from the interruption and get back into their core thought-flow.

Think about that.

Five, minute-long tasks will taint over an hour’s worth of productivity. Your day-to-day life can’t afford that.

5. I Don’t Need Help

For some reason, people see outsourcing as a cry for help. It’s not.

Outsourcing has nothing to do with help and everything to do with being a smart, intelligent and efficient individual who values their most precious resource — time.

How To Use Less To Get More.

(aka The MacGyver Method.)

I spend a lot of time talking to people about decision making. Yesterday, I came up with a pretty cool example that seems to resonate with a particular generation (mine).

So everyone remembers MacGyver right? Super cool guy, terrible haircut, worse fashion sense, But he got shit done with very little.

No one ever said to him, “ Here, go to this Home Depot and pick out whatever you want and do what you gotta do.” No. They said, “Here’s a paperclip and a box of Bisquick. Go make a bomb.”

Limited choices.

You see, we can’t innovate when we have too much at our disposal. As entrepreneurs, we have a lot more freedom than most, and our brains are not wired or comfortable within that broad framework.

So start constructing “Artificially Restrictive Limits” for yourself and your business . Give yourself less to work with, and you will see, almost immediately how the blocks become unblocked and the change happens.

Give yourself the gift of:

Less Time — Bring a project to fruition in half the time you planned. Remember perfect is the enemy of done.

Less Money — What automated or outsourced systems and processes could you put in place if you had to slash 20 percent off your operating budget? The technology is out there right now, find it.

Less Space — Actual physical limits. Use one shelf for your shoes. If your shoes do not fit on the shelf, stop buying shoes.