Sidney Weinberg, the legendary “Mr. Wall Street” and former Goldman Sachs CEO, was a great generator of business deals.

Walter Sachs once called him “the finest professional director in the country.”

Sidney Weinberg started as an assistant to the janitor and worked his way up to become the longest serving senior partner.

He actively sought to be on the board of directors of many companies.

Weinberg eventually held 35 directorships in major U.S. companies like Ford and GE.


Sidney Weinberg started as an assistant to the janitor and worked his way up to become the longest serving senior partner.

He actively sought to be on the board of directors of many companies.

Weinberg eventually held 35 directorships in major U.S. companies like Ford and GE.

Sachs remarked that up 90% of Weinberg’s activity was as a director and that turned out to be very valuable to Goldman Sachs.


He was a true rain maker who funneled relationships and opportunities from corporate America back to his firm.

Rather than simply trying to cold-call prospects or go and vaguely “network” to generate deal flow Weinberg did something far more powerful.

He got in the mix with his prospect universe.

He did business.

It’s called “exploratory business development” – where you conduct ancillary business in order to generate new opportunities. Lateral thinking applied to building deal flow.

He joined boards because it dramatically increased his flow of potential deals –from the companies themselves, from the other directors, and from contacts engaged through those board activities.

That is how executives should think.

Warren Buffett’s famous “buy & hold forever” mantra is itself tied directly into how he develops proprietary deal flow.

The reality is the business and investment world are built around different forms of deal flow.

If you’re not good at generating deal flow then you suffer a major disadvantage to executives who are good at it.

The investment world is predicated on two types of deal flow – generating capital and opportunities to deploy that capital.

Deal flow is the lifeblood of the industry.

Startups often live or die based on their ability to generate deal flow across different aspects of their business.

A critical understanding of how to source and convert quality deals is a make or break skill in business.

The ability to frequently source big deals is what makes an executive a “rain maker”.

The problem is few people have an intelligent framework for how to source deals.

Fewer still, even among top producers, know more than one or two ways to source deals.

Ask many executives how they source deals and you will get generalities like “networking” and “you have to have a pipeline” or “go to conferences”.

None of those answers are wrong.

They are, however, wildly incomplete.

Executive focus should be on building enterprise level deal flow – enough to feed, then scale your organization.

I generally don’t focus on one-off deal generation.

Unless it’s a major, one-time only strategic opportunity or deal.

For example, you only sell your business once. That requires specific opportunity development.

However, you sell to clients every day.

The first step to generating multiple streams of clients is realizing executive function should focus on two areas:

Building deal flow funnels. You have accounting systems, payroll systems, client onboarding systems, and regulatory reporting systems.

Deal flow systems are designed to consistently deliver more clients,  potential acquisition targets, investors, or strategic partners in a way that can be managed primarily by non-executive staff.

For example, if you’re a fund then you might create systemic deal flow by creating a media platform targeting investors to highlight your expertise, investment thesis, and generate investors.

Or creating a regular outreach plan to investor conferences and events to either sponsor or speak (or both).

Systems save you time.

Once your strategy is designed much of the implementation work can be handled by staff.

Chasing small to medium sized single deals is not a good use of your time. That’s why you should systemize as much of that process as possible.

Developing large strategic relationships and major individual deals. Major strategic alliances, “whale” clients, and large distribution opportunities require individual attention.

It’s not the best use of time for top level executives to focus on simply closing one small to medium size client after another.

Sidney Weinberg’s approach of gaining 35 directorships is a wonderful example of a strategy capable of delivery on both areas.

He delivered both major clients and transactions.

And created a network of relationships and opportunities he could funnel back to his firm.

What’s missing for most executives is a comprehensive plan on how to build a pipeline of targeted deals.

Figuring that out starts with understanding your business ecosystem.

If you don’t have a clear view of how deal flow can be generated in an industry, then you cannot create a system to generate deal pipelines.

The most obvious place to look is

One of the easiest ways to begin thinking about this is to look for hubs of potential clients.

Places where your prospects congregate.

There are obvious opportunities like industry events, business associations, and industry media sources.

Often, the most productive sources or the not-so-obvious opportunities.

Like the vendors who service your prospect group.

You’re looking for the natural hubs of potential prospects

If you think in terms of simple networking, then business advisors who service your prospect group are a strong source.

For example, law firms specializing in your target industry will have a strong network you could leverage.

Major suppliers, logistics providers, accounting firms, auditing firms, advertising agencies, and many other types of firms can become a source of new deals.

But the great rainmakers create new avenues of opportunities.

Like Sidney Weinberg, they approach deal flow in fresh, innovative ways.