Webinar Recap: Sales Lessons from the Trenches of a $50M Raise with Keeley Hubbard
What does it really take to raise $50 million?
According to Keeley Hubbard, it takes a lot more than a strong investment opportunity and a polished presentation.
During Momentum Multifamily’s August 12 webinar, “Sales Lessons from the Trenches of a $50M Raise,” Keeley shared the lessons she learned from nearly two decades in capital raising and sales—including her experience raising more than $50 million for a pre-IPO technology company.
The raise was anything but ordinary. Investors were required to sign NDAs, webinars were limited to small groups, recordings weren’t permitted, and for a significant portion of the raise, the company, founder, and executive team couldn’t even be disclosed.
With no mass marketing strategy to fall back on, the raise depended heavily on one thing: having real conversations with investors and knowing how to lead those conversations.
The lessons Keeley shared apply well beyond tech. For multifamily operators, fund managers, and anyone raising private capital, her approach offers a practical look at what it takes to build investor confidence, handle objections, and keep moving when a raise gets difficult.
The Messy Middle Is Where Most Raises Get Difficult
One of Keeley’s biggest reminders was that every capital raise eventually hits what she calls the “messy middle.”
The beginning is exciting. You have new commitments coming in, investors are engaged, and the momentum feels real.
Then things slow down.
Maybe you’re 30% or 40% funded and suddenly the phone isn’t ringing. Investors who seemed interested aren’t responding. The excitement of the launch has worn off, and it’s easy to start questioning whether you’ve misjudged the opportunity.
Keeley’s advice: Don’t confuse silence with rejection.
Investors are busy. Your deal may not be their immediate priority. Sometimes they simply need more information or another conversation before making a decision.
She also recommended replacing the typical “just following up” message with something more direct:
“What information do you need from me? What questions do you have to give this a green light or a red light?”
Giving an investor permission to say “no” can actually make it easier for them to tell you what’s really holding them back—and that’s much more valuable than another vague “I’ll think about it.”
Stop Selling for Approval. Start Leading.
One of the strongest themes throughout the webinar was the difference between customer service energy and leadership energy.
As capital raisers, it’s easy to fall into the trap of trying to make every investor happy. You answer every question immediately, over-explain your deal, accommodate every request, and chase investors who aren’t making a decision.
Keeley’s perspective is different.
Investors don’t need you to be their salesperson. They need you to be their leader.
That means being confident in your investment thesis, your structure, your fees, and your expectations.
It also means being comfortable when someone doesn’t agree with you.
Keeley shared multiple examples of investors pushing for different economics, additional access, or special treatment. Her response wasn’t to immediately negotiate.
It was to explain the structure and stand behind it.
That doesn’t mean being inflexible or dismissive. It means knowing what you’re willing to change—and what you’re not.
Don’t Be Afraid to Lose an Investor
This may be one of the hardest lessons for a capital raiser to internalize:
You have to be willing to lose the investor in front of you.
Keeley shared an example involving a family office representative who asked what he would receive in exchange for writing a larger check.
Her answer was essentially: nothing beyond the terms already established for the deal.
In another situation, a billionaire investor offered to fund approximately $10 million of the remaining raise, but wanted board seats, direct access to the founder, and extensive access to proprietary information.
Those requests didn’t fit within the structure of the investment.
Keeley said no.
The interesting part? The investor kept coming back.
Her point wasn’t that every investor will respond this way. It was that holding your boundaries can increase credibility rather than hurt it.
When you immediately change your deal every time someone pushes back, sophisticated investors may see that as a lack of conviction.
Sometimes the most valuable thing you can communicate is that you’re willing to walk away from money that isn’t a good fit.
Objections Are Buying Signals
Another important shift Keeley encouraged is how capital raisers think about objections.
Instead of viewing an objection as something that needs to be overcome, look at it as evidence that the investor is still engaged.
If someone says:
- “I don’t like the hold period.”
- “I’m not sure about the market.”
- “The minimum investment is too high.”
Don’t immediately launch into a defense of the deal.
Instead, isolate the concern.
A simple question like:
“Is that the only thing that’s making you hesitant about investing?”
can uncover a much bigger picture.
The investor may reveal that they’re also unfamiliar with the market, don’t understand the asset class, or have another concern they haven’t mentioned.
Now you can address the actual issues instead of trying to solve the wrong problem.
Keeley also stressed the importance of being honest about risk.
During the pre-IPO raise, she wasn’t afraid to tell investors that the investment was high risk and that they shouldn’t invest more than they were comfortable losing.
That kind of honesty may sound counterintuitive in a sales conversation, but it builds credibility.
You don’t build trust by pretending risk doesn’t exist. You build it by being willing to talk about it.
Emails Don’t Close Deals. Conversations Do.
Another major takeaway from the webinar was the importance of getting out from behind the keyboard.
Emails are useful. Webinars are useful. Investment materials are useful.
But they aren’t substitutes for conversations.
Keeley emphasized that capital raising is ultimately a relationship business. Investors need opportunities to ask questions, express concerns, understand the opportunity, and decide whether they trust the person on the other side of the table.
Her mindset was simple:
“When I’m on the phone, money moves.”
That doesn’t mean every phone call results in a commitment. It means that real conversations create opportunities to discover what’s actually keeping an investor from making a decision.
For a capital raise, that can mean hosting multiple live webinars, offering different opportunities for investors to attend, and intentionally moving interested prospects into one-on-one conversations.
Your Minimum Investment Says Something About Your Deal
Keeley also challenged attendees to think carefully about their investment minimums.
She shared examples of fund managers with dramatically different minimums and fundraising results. One manager had a $25,000 minimum and raised approximately $300,000. Another had a $250,000 minimum and raised approximately $4.2 million.
The point wasn’t that raising the minimum automatically produces more capital.
The point was that your minimum communicates something about your offering and the type of investor you’re trying to attract.
A low minimum can create a large number of small investors, which may require just as much—or more—time and effort to manage.
It can also unintentionally signal to larger investors that the opportunity isn’t designed for them.
Keeley’s recommendation was to establish a minimum that reflects the quality of the opportunity and the investor base you’re trying to build.
If an individual investor genuinely needs a different arrangement, that conversation can happen privately.
But don’t undermine your own positioning by announcing your minimum and immediately explaining how easy it is to get around it.
Don’t Negotiate Against Yourself
The same principle applies to fees and splits.
Keeley shared a story about a fund manager who presented an 80/20 split. An experienced executive questioned whether the economics were too favorable to the manager.
Instead of confidently explaining the rationale behind the structure, the fund manager immediately offered better economics to investors.
The investor still didn’t invest.
Meanwhile, the fund manager had permanently reduced his own economics.
The lesson is straightforward:
Don’t negotiate against yourself.
Investors expect fund managers and operators to make money. In fact, good investors should want the sponsor to have meaningful economic incentive to perform.
Know why your fees, splits, and performance incentives exist. Be prepared to explain them. And then stand behind them.
Capital Raising Is a Roller Coaster
Keeley closed with a message that may have resonated with anyone who has raised capital:
The emotional ups and downs aren’t going away.
You’ll have investors who say yes and then disappear.
You’ll have deals that appear to be oversubscribed only to develop a multimillion-dollar gap days before closing.
You’ll have people delay decisions, change their minds, or stop responding.
The question isn’t whether those things will happen.
The question is how quickly you recover when they do.
Keeley talked about avoiding what she calls the “cute quit”—the moment when you convince yourself that you’ve done well enough to stop pushing.
For example, if your goal is to raise $25 million and you’re sitting at $15 million, it can be tempting to tell yourself, “$15 million is still great.”
And it is.
But if there’s still time to reach $25 million, don’t mentally quit before the raise is actually over.
Keeley shared how, during one particularly difficult stretch, she and her business partner pulled out written affirmations and read them aloud to reset their mindset.
Whether or not affirmations are part of your personal routine, the underlying lesson is important: pay attention to the story you’re telling yourself during the difficult parts of a raise.
Your mindset can influence your actions long before the final numbers are on the scoreboard.
The Network Doesn’t End With Friends and Family
During the Q&A, Keeley also addressed what happens when you’ve exhausted your personal network.
Her answer: go meet people you don’t know.
She encouraged capital raisers to look beyond traditional networking events and intentionally put themselves in environments where they can build new relationships—from nonprofit events and private clubs to affinity groups and other communities where high-net-worth individuals spend their time.
And when someone asks what you do, be intentional about how you explain it.
Saying “I’m a real estate investor” can lead people to assume you’re a fix-and-flip operator.
Instead, Keeley suggested positioning yourself around the business you actually run—for example, describing yourself as someone who runs a private investment firm or private investor community.
Then focus the conversation on the problems you help solve.
Are investors concerned about market volatility? Looking for alternatives to the stock market? Interested in tax-advantaged private investments?
Lead with the problem, then explain how you help.
The Bigger Lesson: Capital Raising Is a Sales Profession
Perhaps the biggest takeaway from Keeley’s presentation was that capital raising is sales.
A great investment opportunity matters. A strong track record matters. A polished presentation matters.
But none of those things eliminate the need to sell.
Successful capital raisers need to be able to communicate clearly, ask good questions, handle objections, have difficult conversations, maintain conviction, and continue moving forward when things don’t go according to plan.
Most importantly, they need to lead from a place of confidence rather than scarcity.
For multifamily operators and private-market fund managers navigating a more selective capital environment, those skills have become increasingly important.
The goal isn’t to convince every investor to invest.
It’s to find the right investors, communicate the opportunity honestly, build trust, and have enough conviction in your business to know when to stand firm.
That was the real lesson from Keeley’s “Sales Lessons from the Trenches of a $50M Raise.”
Raise with confidence. Have the conversations. Tell the truth about the risk. And don’t be afraid to hear “no.”
Thank you to Keeley Hubbard for sharing her experience and hard-earned lessons with the Momentum Multifamily community.