- Jeff "Fuzzy" Wenzel
- Posts
- The Founder’s Playbook for Raising in a Market Held Together by Duct Tape and Vibes
The Founder’s Playbook for Raising in a Market Held Together by Duct Tape and Vibes
Raising capital right now feels like pitching inside a pressure cooker—here’s how smart founders are still closing rounds fast.
Learn from this investor’s $100m mistake
In 2010, a Grammy-winning artist passed on investing $200K in an emerging real estate disruptor. That stake could be worth $100+ million today.
One year later, another real estate disruptor, Zillow, went public. This time, everyday investors had regrets, missing pre-IPO gains.
Now, a new real estate innovator, Pacaso – founded by a former Zillow exec – is disrupting a $1.3T market. And unlike the others, you can invest in Pacaso as a private company.
Pacaso’s co-ownership model has generated $1B+ in luxury home sales and service fees, earned $110M+ in gross profits to date, and received backing from the same VCs behind Uber, Venmo, and eBay. They even reserved the Nasdaq ticker PCSO.
Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.
The Founder’s Playbook for Raising in a Market Held Together by Duct Tape and Vibes
Jobs numbers last week were wild.
People keep calling for a recession, but somehow the economy is still standing, barely.
From the frontlines, here’s what we’re seeing in startup fundraising:
Deals are taking 40% longer to close
Investors are skittish unless you're solving an immediate, high-urgency problem
Budgets tightened overnight, and now you're not just pitching—you’re in a knife fight with every other founder and fund manager for attention.
When markets become uncertain, most founders tend to pull back.
They go generic.
Try to sound “investable” to everyone.
Water down their story so they don’t risk getting a no.
That’s a mistake.
When investors are scared about capital risk, they tend not to look for the cheapest deal.
They look for the most certain bet.
And “maybe this will work” is off the table.
Here’s what’s working now:
1. Specificity Wins Rounds
Vague pitches die fast in this market.
Your startup isn't “building AI for healthcare.”
You’re “building an FDA-compliant AI triage system that reduces average ER wait times by 29% in under 90 days.”
That specificity makes you investable.
It tells the investor:
Who this is for
What problem it solves
How it solves it
What the outcome looks like
The best founders are nailing:
Problem + Person + Promise + Proof + Process
Miss one, and you sound like everyone else.
2. Use AI Where It Adds Leverage, Not Where It Dilutes Trust
Don’t pitch your use of AI like it’s the product.
Investors are getting hundreds of decks with “AI” as a buzzword.
Use AI to do what it’s good at:
Organize your CRM
Personalize outreach
Automate pitch follow-ups
But your strategy, narrative, investor engagement, and vision?
That’s your job as founder.
That’s what gets funded.
3. Shift the Value Conversation
Innovative founders aren't lowering prices or valuations.
They're reframing the comparison.
Example:
“Right now, you’re spending $300K/year on a marketing team trying to generate qualified leads.
What if we could generate that same volume of investor-qualified traffic for $18K, freeing your team to focus on closing checks?”
You're not an expense.
You're an efficiency layer.
A multiplier on capital already being deployed.
4. Know How Investors React Under Stress
You’re dealing with two types of buyers:
Chunk-Up Thinkers (Strategic Investors):
They want one startup that solves multiple problems.
Pitch the broad vision, the category creation, the future ecosystem play.
Chunk-Down Thinkers (Risk-Averse Angels or Syndicates):
They want clear, narrow, measurable wins.
Pitch them the next milestone, the product launch, the channel proof.
Tailor your story to their risk psychology.
This one insight can double your close rate.
5. Build Leverage Through Trust, Not Hype
The best founders right now are doing “no-ask check-ins” with past investors, warm leads, and aligned operators.
They’re listening.
They’re helping.
They’re showing up—without pitching.
Because when capital unlocks again, trust becomes the filter.
Investors will ask:
“Who already understands our thesis?”
“Who’s been in the loop?”
“Who’s clearly obsessed with solving this problem?”
In a market like this, certainty is the most valuable asset you can offer.
Not certainty of outcome, no one believes that.
Certainty of understanding.
Certainty of commitment.
Certainty of fit.
That’s why we built four distinct offerings to help founders raise now, not later:
Kickizer – Investor research and targeting engine
Invst Guru – Investor-facing thought leadership and newsletter distribution
Pre-IPO Hype – Full-funnel growth marketing for equity crowdfunding
Verified Angel Investors – Direct intros to active accredited investors
If you’re raising capital right now and getting friction at every step, let’s change the narrative.
Let’s help investors say yes faster, with certainty.
Voice AI Security That Impacts Your Bottom Line
Learn how enterprise IT and ops leaders are using compliance to unlock Voice AI scale—deploying faster, reducing risk, and accelerating procurement.
This guide shows why HIPAA, GDPR, and SOC 2 are now deal-makers, not blockers. From securing PHI to routing across 100+ sites, see how security-first platforms reduce friction and enable real-world rollout across healthcare, insurance, and more.
Reply