September 30, 2023
Read time: 3 minutes

A couple weeks ago I attended a conference in Cleveland, Ohio.

Over 100 founders of multi-asset holding companies met to exchange ideas.

It was a highly diverse group of leaders with representatives across the US, South America, Europe and Asia.

Despite the diversity, everyone shared a common outlook on business, namely the value of uncorrelated cash flow, extreme accountability and long-term compounding — pillars of what makes for a successful Holding Company.

Last week I shared a few themes that emerged from the conference:

  • Find great people, align incentives and spoil them with autonomy.
  • Fear of missed opportunity can be a powerful motivator.
  • Ideas are plentiful, execution is hard.

Today, I want to get tactical and offer specific ideas on two topics everyone was talking about:

  1. Artificial Intelligence
  2. Offshore Talent

Let’s go:

The Great Divide

I attended a small group session focused on the way operators are leveraging technology in their portfolio companies.

In general, Generation X and Baby Boomer attendees had objectively larger Holding Companies.

However, their comfort with technology, and specifically artificial intelligence, was far less than the younger attendees.

The chasm between these two groups was much wider than I expected.

One gentleman summed it up well:

“I need someone to audit my businesses, identify workflows that could benefit from AI, explain the financial return on investment, and then just implement it. I don’t want to learn how it works, I just want it done.”

His tone was filled with underlying anxiety.

He needs help and isn’t afraid to pay top dollar for it.

In fact, for anyone with a background running agencies, I think there is a compelling opportunity to build a firm focused on this thesis.

If this idea resonates with you, send me an email and let’s brainstorm.

Separately, many of the younger attendees were already leveraging AI in their businesses.

Common use cases include improving internal communications and overcoming human error.

Some specific examples:

  • When a new sales lead is received via email, a zap is triggered (using Zapier) to push the contents of the email to ChatGPT. GPT scans the contents and pulls relevant info into a standard text summary. That summary is then automatically sent to relevant team members and simultaneously cataloged in the company’s CRM.
  • A field agent for a home services business completes a quote at the job site. Once he submits the form, ChatGPT scans it and cleans up all formatting/grammar errors. It also flags any missing information. The field rep then provides the missing info and a clean invoice is automatically generated and sent to the customer (without a manager ever reviewing it).
  • A sales rep calls a phone number at the end of the day and leaves a 2 minute voice message. The message includes who she spoke with, what they spoke about, important next steps, etc. Software is used to transcribe the voice recording. The transcription is sent to ChatGPT, which again scans the information and sends back a template summary to the rep’s manager.

I came away all the more convicted in the opportunity to apply modern technology to Main Street businesses.

Even the big boys are far behind.

Global is the New Norm

The conversation around global talent wasn’t, “should we be leveraging VA’s?”

Instead, it was, “where do we find the best offshore talent and how do we equip them to be successful?”

One attendee runs a management consulting prep firm run by his 30 offshore employees. The business is nearing 8-figures of annual revenue with just a handful of US workers.

A few insights:

  1. Geographic Centers: India is the best location for hiring accountants and bookkeepers. Sri Lanka / Taiwan for hiring engineers. The Philippines for customer service. Most people source talent directly using Upwork or onlinejobs.ph.
  2. Compensation Strategy: Pay offshore workers monthly using a service like Wise. Offer 90% of fair market value for the first 90 days, then increase to 100% of market. Over time, gradually raise to 120% of market. Creates a clear progression, which keeps folks motivated.
  3. The Small Things Matter: Go above and beyond to reward your best offshore employees. Small gestures like meal stipends, wellness days, or team swag can go a really long way to improve retention.

Between the combination of technology automation and offshore talent, operational efficiency was a major theme throughout the conference.

The goal should be to make our US employees most productive by allowing them to focus on the highest ROI work.

So was the $5,000 conference worth it?


The learnings were great, but the real value was in the people I met.

Plus, it’s so easy to feel isolated in a world dominated by remote work.

Professional interactions can feel very transactional.

More than 5 minutes of “pleasantries” in the beginning of a 30-minute zoom meeting and we start to get antsy.

Feelings of unproductivity creep in.

So the HoldCo Conference was a nice change of pace.

Most attendees were down to earth and looking for real connection.

Conversations weren’t rushed.

There was space to get to know one another other.

I think we can all use a bit more of that these days.

See you back here next week,


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