by Jason Seward
We just got back from the Dealmaker Event Richmond.
300+ people.
3 straight days.
Speakers all day. Conversations in every corner. Late nights. Early mornings.
It’s the kind of environment that feels like opportunity is everywhere… and somehow you still leave wondering if you actually moved the needle.
Here’s the reality:
You are not there to meet everyone.
You are there to meet the right people.
And if you don’t have a strategy going in, the event will run you over.
The Biggest Mistake: Treating It Like Speed Dating
Most people walk into these events with one goal:
“Meet as many people as possible.”
That sounds productive. It’s not.
You end up having 40 surface-level conversations, collecting a stack of business cards, and remembering exactly none of them a week later.
Quantity feels good in the moment.
Quality is what actually pays you later.
Step 1: Define What a “Win” Looks Like Before You Walk In
If you don’t define success, your brain defaults to chaos.
Before the event, ask yourself:
- Am I looking for borrowers?
- Investors?
- Strategic partners?
- Just education?
Now narrow it down further:
👉 “If this event goes perfectly, I leave with ______.”
Examples:
- 3 serious borrower relationships
- 2 potential capital partners
- 1 operator I can collaborate with
That’s it.
Not 30. Not 50.
3–5 meaningful connections beats 50 forgettable ones every time.
Step 2: Play Offense, Not Defense
Most people sit back and wait for conversations to come to them.
Bad move.
The people you want to meet are doing the same thing you should be doing… being intentional.
A few ways to play offense:
- Identify speakers or attendees you want to meet ahead of time
- Be willing to walk up and start the conversation
- Don’t overthink the opener
Simple works:
“Hey, I heard you mention ____. I’d love to hear more about that.”
You don’t need a clever line. You need to start.
Step 3: Have a Clear, Non-Cringey Way to Explain What You Do
When someone asks, “What do you do?”… most people ramble.
You’ve got about 10 seconds before they mentally check out.
Keep it simple and clear:
“We lend on fix & flip deals. Short-term loans, move fast, and structure deals around the numbers.”
That’s it.
If they’re interested, they’ll ask more.
If not, move on.
Clarity beats cleverness.
Step 4: Go Deep, Not Wide
This is where most people miss.
When you find someone aligned:
- Stay in the conversation
- Ask better questions
- Actually listen
Good questions:
- “What kind of deals are you focused on right now?”
- “Where are you getting stuck?”
- “What does your business look like over the next 12 months?”
Now you’re not networking.
You’re building something.
Step 5: Manage Your Energy Like It Matters (Because It Does)
These events are a grind.
Long days. Constant talking. Late nights. Early mornings.
If you don’t manage your energy, you’ll be useless by Day 2.
A few rules:
- You don’t have to go to everything
- It’s okay to step away and reset
- Not every late-night hang is worth it
The highest ROI conversations often happen when you’re sharp, not when you’re running on fumes at midnight.
Protect your energy like it’s part of your strategy… because it is.
Step 6: The Follow-Up Is Where the Money Is Made
This is where 90% of people drop the ball.
They meet great people… and then do nothing with it.
Within 24–48 hours:
- Send a quick message
- Reference something specific from your conversation
- Keep it simple
Example:
“Good meeting you in Richmond. I liked what you said about ______. Let’s stay in touch—would love to see how we can work together.”
No follow-up = wasted event.
Step 7: Measure the Event the Right Way
Don’t judge success by:
- Number of people you met
- Number of cards you collected
Judge it by:
- Number of real relationships started
- Quality of conversations
- Opportunities created
One great relationship can change your business.
50 random conversations won’t.
Final Thought
Networking events like the Dealmaker Event are massive opportunities.
But only if you approach them with intention.
Otherwise, they’re just three exhausting days of talking.
Be selective.
Be intentional.
Play the long game.
That’s how you actually win in rooms like that.
If you are local to the Hampton Roads Market, consider joining us at our April 7th event where we will focus 100% on networking. It will be a good opportunity to put all of the above into practice at a smaller event. See link below for more information.