Today’s Tom Sawyer

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Written By Bill Eisenhauer

Bill is a technologist, marketer, and microentrepreneur who helps people transition from trading time for money to building a portfolio of cash-flowing digit assets.


  • What you can learn from Tom Sawyer to gain back your freedom
  • What it means to be a toll collector and how to occupy toll position
  • Two inspiring examples of toll position

Today’s Tom Sawyer has invaded your space and is getting by on you.

And me…

I’m in no rush to decipher that little riddle until I tell you a story.

Ever read Mark Twain’s, “The Adventures of Tom Sawyer?”

All Work and No Play

Back in the days before laptops and smart devices…before cars…before practically every bit of convenience that you and I take for granted, there was a 12-year-old boy named Tom Sawyer.

On a Summer Saturday morning not unlike the day this newsletter was published, everyone around St. Petersburg, Missouri was in a great mood and the town was brimming with life.

Except for Tom.

You see, Aunt Polly had chosen this exact day to punish Tom for all his mischievous antics.

He had plotted and executed one prank too many!

And so on this glorious Saturday morning with the locust trees in bloom and the fragrance of blossoms filling the air, he was sentenced to whitewashing the fence.

Think of whitewashing like painting the fence white.

Tom was not too excited about losing his freedom today or any day, so he hatched a plan.

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All Play and No Work

As Tom considered his situation while making those first careful whitewash strokes, a friend wandered by boasting of his carefree plans for the day.

But Tom continued painting with flamboyant flourishes and a convincing air of joy.

He was convincing enough that his friend felt like there was something he was missing and requested to take a turn.

Tom considered for a moment but denied the request—Aunt Polly had a standard and this friend just couldn’t be trusted to measure up. This job needed to meet with Aunt Polly’s approval!

That was the story at least.

After some grumbling, the friend sweetened the deal by offering Tom an apple for a turn.

Tom took the deal, of course.

And while his friend worked, Tom took it easy and ate the apple.

As morning turned into afternoon, Tom made deal after deal with different friends as they passed by; each time piquing their interest and creating insatiable intrigue.

Somehow he was trading his day’s chore for their treasures!

And when the day was done, his punishment had been completed by others and he had accumulated a good bit of their stuff.


Be a Toll Collector

I wouldn’t tell you that story if I didn’t think you and I could use our resourcefulness and abilities to turn a chore into a triumph.

So how do you accomplish this holy grail of getting paid while other people do your work?

The big concept is to create a situation where you are in a toll position; becoming a toll collector for a value exchange that you’ve created.

But the key is that you are not involved in the value exchange—you just get paid.

Now this isn’t strictly what Tom was going, but the net was the same; his friends did the work for Aunt Polly and he accumulated treasures.

Opportunity Spotting

As is a recurring theme in these newsletters, you need to strap on your opportunity goggles and become a deal alchemist.

You need to find two or more parties that are complementary to each other, but who lack the creativity to see the opportunity themselves.

You approach one party with the idea and tie up the “rights” to offer their part of the value exchange to another party.

You do the same with the other party.

Your arrangement then permits the value exchange to happen; each side gets what they want while also providing profit for you.

The profit is the “toll” that you collect as you occupy the toll position in the deal.

A Real Example

Here’s an example from the real estate investing world.

There are people known as wholesalers who put properties under contract with sellers who need to sell their homes without a traditional realtor.

Wholesalers do not ever intend to buy properties themselves, they instead want to flip the contract to an investor; picture the investor being a fix-and-flipper.

The major struggle for the wholesaler is to find that actual buyer.

If they find no buyer before the contract expires, there will be no profit!

So what the wholesaler really needs to do is find properties and curate a large buyer list. Trouble is, many wholesalers have a weak buyer list.


If I focus on accumulating a massive buyer list, I am able to match the wholesaler up with a buyer and take a portion of the profits.

I didn’t go out and find a house—that’s hard and time-consuming!

I did a little bit of work over a period of time to build a buyer list and a wholesaler list—just emails and phone calls!

So for building the digital assets of a buyer list, a wholesaler list, and a matching site, I collect a finder’s fee and leave them to do all the work.

A More Digital Real Example

A course creator has created a course and has an extensive customer list.

The course dovetails nicely with a few software-as-a-service offerings, but the course creator is focused narrowly on their course and doesn’t see the partnership opportunity with the SaaS companies.

You license the rights to offer SaaS subscriptions to the course customers; getting paid on a recurring basis as subscriptions are paid for.

You automate the whole process and it just works and you get paid into perpetuity.

Wrapping Up…

It’s been 40+ years since Rush released Tom Sawyer but I’m co-opting the opening stanza to wrap this up:

A modern-day warrior
Mean, mean stride
Today’s Tom Sawyer
Mean, mean pride

A modern-day warrior fights for their freedom and the ability to live an authentic life.

I’ve given you a concept and a couple of ideas.

Start small, nail it, then scale it.

Live long and prosper.

— Bill

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