Technology

How to fundraise like a Special Forces commander

Military vet and founder of SOLO runs a platoon of assistants, assembles target packages

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As an Army Special Forces detachment commander in Iraq, Tommy Sowers was charged with persuading actors of all stripes to cooperate with the U.S. military.

“Some of them wanted to kill us, but you had to find out how to get them to work with us,” Sowers said of building rapport with different elements.

That experience, along with a number of other stints that required him to win over strangers, has taught him quite a bit about how to build relationships.

All of this know-how comes in handy when he’s pitching investors on his real estate tech startup, SOLO, which hopes to popularize a menu-style business model for agents.

Here’s how a Green Beret wages a funding campaign.

1. Assemble a platoon.

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This may not be an option for all startup founders, but if you have a group of supporters willing to help you build your business, take full advantage of them.

Sowers has put together “the equivalent of a Special Forces team,” he says. It’s made up primarily of 20-somethings whom Sowers taught at West Point, where he was once an assistant professor.

nathan solo

‘Horde’ member Nathan Ramia

Nathan Ramia, one of the team members, says he and other helpers, who are unpaid, think of working for Sowers as a “next step in mentorship” from the Army vet.

“We call ourselves the ‘Horde’ because what we do is really more educational,” Ramia said. “We currently sit about 20-strong, organized like a platoon.”

2. Create ‘target packages’

Applying a tactic used by the Special Forces, Sowers has his team put together “target packages” on everyone Sowers has met or ever plans to meet. Every package is packed with information that paints a detailed portrait of an individual.

During his first deployment in Iraq, Sowers said he had a lot riding on the quality of such packages.

“These were local political leaders, sheikhs, Iraqi army and police, insurgents that wanted to flip sides, insurgents that wanted to kill me,” he said. “So it really was life or death on knowing what I was walking into.”

Target package on Teke Wiggin


Sowers’ “target package” on me. (I don’t know how a ‘Horde’ member found out I like karaoke.)

The “Horde” creates target packages by pulling information from social media accounts, online bios and other Web content that captures an individual’s day-to-day, history and interests.

One crucial piece of information for target packages on investors is a summary of their “investment thesis,” the principle that guides how a firm chooses what companies to back.

Armed with an in-depth profile on a contact, Sowers can go into a meeting with a nuanced understanding of what makes a person tick.

In meetings with investors, Sowers also benefits from projecting confidence, partly a result of the fact that — in contrast to some of his meetings with local players in Iraq — “nobody is trying to kill me.”

Left to right: Brendan Syron, Tommy Sowers, Brad Harrison, John Ryu

Left to right: Brendan Syron, Tommy Sowers, Brad Harrison, John Ryu

Sowers presenting SOLO to the venture capital firm Scout Ventures.

3. Fortify relationships.

After meeting with someone, Sowers takes steps to build goodwill and ensure he’s better prepared to engage the person in the future.

Sowers immediately dictates notes about a meeting after it wraps up (using the app Evernote), and then has his team draft thank-you letters to people part of the meeting. Later, he reviews the drafts, adds any necessary tweaks and sends them off.

4. Perfect your pitch.

To raise the odds of securing funding, you should consider reaching out to as many prospective backers as possible.

Sowers has learned exactly what to say and how to say it when he contacts potential investors for the first time, maximizing his chances of piquing their interest.

“Fair to say that the objections — like in real estate or in political fundraising — fall into broad buckets,” he said. “Just like anything, you learn what works and what doesn’t.”

Sowers has leaned on one of his co-founders, a real estate agent who’s sold more than $200 million in real estate, to learn how to hone and implement his phone pitch.

5. Call for backup.

You probably don’t have Sowers’ social network.

After all, you weren’t a congressional candidate, Special Forces commander, assistant secretary of the Department of Veterans Affairs, McKinsey management consultant, or professor at Duke University and West Point.

But if you were, you could leverage a wide array of contacts for advice and introductions to potential investors, just like Sowers has.

During a single day in New York City, Sowers recently pitched the head of a venture capital firm whom he met at a veterans’ event; met a former classmate, who, like Sowers, also ran for congressional office and heads up a tech startup; and powwowed with the co-founder of the educational institution General Assembly, Matthew Brimer.

He wrapped things up by attending an exclusive event focused on how technology could advance campaign finance reform.

6. Arm yourself.

Sowers dictates and organizes his notes using Evernote; he packs a separate phone battery charger in his laptop bag; he always sports leather boots (his fondness for the footwear stems from his Midwestern roots and military background); and he wears a suit.

Why the suit?

Because in real estate, professionals often wear suits, not T-shirts.

The people who wear T-shirts, Sowers says, are often those starry-eyed founders who charge into real estate with little knowledge of how the industry works and fall flat on their faces.

“The ash heap of history is littered with startups … with just the consumer in mind,” he said. “What makes [SOLO] unique is we are both pro-buyer and pro-agent.”

Email Teke Wiggin.