Trust is built the same way everywhere: one honest conversation at a time, long before a founder ever asks for money. That is the short answer. A deeper explanation came out of an Outside In conversation between moderator Derrick L. Maultsby Jr. and Damian Murray, an investor and strategist at Level Up Ventures, the pre-seed and seed-stage fund backed by media giant Hearst.
Outside In exists for exactly this reason. Rather than staying inside Pittsburgh’s own network, Innovation Works built the series with the guidance of venture attorney Derrick L. Maultsby Jr. to fly investors from Derrick’s national network into the city and put them directly in front of local founders. This installment took place on August 4, 2026 at Tech Forge in Lawrenceville.
For founders raising a pre-seed or seed round, and for the community builders trying to get them investor-ready, that conversation produced six lessons worth carrying forward.
How Outside In came to be
Jane Joseph, Innovation Works’ Director of Communications and Community Development, opened the night with the origin story: a complaint turned into a solution. She had been telling Derrick there needed to be a better way to connect investors to the founders building in southwestern Pennsylvania. Derrick’s response was to challenge her to actually build one, and to offer his own national investor network to make it happen.
Derrick, a Managing Associate at FBT Gibbons who splits his time between Pittsburgh, New York, and Nashville, framed the mission plainly: Pittsburgh has no shortage of people complaining that there isn’t enough investment in the city, but complaining doesn’t fix anything. So instead, he started bringing investors here himself.
Who Damian Murray is, and where Level Up Ventures invests
Damian’s path to venture wasn’t a straight line. Born in St. Louis and raised in Columbus, Ohio, he studied finance at Jackson State University before going to work for a founder named Dawn Dickson, whose vending-machine software startup, Pop Comm, became one of the first companies to raise significant crowdfunding, eventually pulling in $3 million and helping influence changes in crowdfunding legislation along the way. That experience showed Damian a gap in venture capital: not enough investors understood the problems that diverse founders were solving.
From there, his career took him through a fellowship at Columbia, venture internships at Microsoft’s fund and elsewhere, a year in Beijing as part of the Schwarzman Scholars program (including time at ByteDance), and a stint at Volvo Cars working on corporate strategy and venture investing across the U.S. and Europe. After three years abroad, he came home and joined Level Up Ventures, part of the Hearst family of venture funds.
Damian explained how three venture funds operate out of Hearst: Hearst Ventures (its legacy fund, writing larger, later-stage checks usually Series B and up), Hearst Lab (focused on women-led founders at seed and Series A), and Level Up itself, which writes pre-seed and seed checks, generally $300,000 to $500,000 with follow-on capacity, specifically for founders who have historically had less access to capital. Level Up invests across fintech, sustainability, sports and media, healthcare, and supply chain and logistics. Damian personally focuses on fintech, sustainability, and sports and media, drawing in part on Hearst’s roughly 9 to 10% ownership stake in ESPN.
Lesson 1: Your Online Presence Is Doing More Work Than Your Deck
Level Up reviews something like 400 deals a year, so the natural question is what separates the decks that get a second look from the ones that don’t.
Craftsmanship matters. A deck that’s clearly and visually organized signals how seriously a founder is taking the raise, and an investor should be able to understand the story without having to work for it. But Damian pointed to something founders underestimate: most investors, especially at the earlier stages, still source the majority of their best deals themselves, through LinkedIn, in-person meetings, or their own networks, rather than through cold inbound. Building a visible, active online presence isn’t optional. Posting about what you’re building and letting your expertise show through consistently is often what gets a founder noticed before they ever send a deck.
Derrick backed that up with an anecdote: a well-networked client of his posted a product announcement video on LinkedIn, walking through the thesis, the market, and the forecast, and ended the day with 99 investors in his inbox. The lesson isn’t “post a viral video.” It’s that relationship-building compounds, and it pays off exactly when you need it to.
Lesson 2: Consistency Is the Real Diligence Test
Level Up does invest in solo founders, but Damian was clear about the bar: a solo founder generally needs to combine technical ability with real business and sales acumen, a combination that’s genuinely rare. He described a recent deal where a founder’s former co-founder left because he couldn’t communicate with Latin American medical providers in Spanish; the remaining founder could handle both the product build and the customer-facing sales work himself, which is what made him fundable solo.
On the diligence side, a few things reliably kill a deal for Damian. Founders who tell one story to him and a different story to his managing partner top the list. Level Up records all of its sessions, and Damian was candid that most investors are recording and transcribing conversations with founders, so inconsistencies get caught. Numbers or claims that don’t hold up under scrutiny, like a “closing” round that turns out to still be actively fundraising, also raise immediate red flags, not necessarily because the news itself is disqualifying, but because it damages trust in what the founder is telling them.
And then there’s plain old annoyance. Sending five or ten LinkedIn messages, texting an investor’s personal number repeatedly, or following up excessively after a meeting reads as a lack of respect for other people’s time and bandwidth, and it colors how an investor remembers a founder even if the underlying business is sound. Level Up’s standard: they commit to responding to every founder either way, so founders don’t need to chase an answer.
Lesson 3: The Relationship Doesn’t End When the Check Clears
Damian broke down three types of founders post-investment. The best ones treat their investors as active team members, reaching out for intros, helping landing customers, and being specific about what they need. A second group communicates sporadically but consistently. The third group goes fully dark, sometimes for six or seven months, even when information rights exist in the deal documents.
He offered a strong example of a portfolio company doing this well: Growth Sync, which realized Hearst had a large, often-empty event space in its New York City building and asked to use it, hosting a 50-person event during New York Tech Week that brought together customers and investors. It worked so well that Level Up is now rolling the idea out across its whole portfolio. Once an investor is on your cap table, they’re not just a source of capital. They’re a resource to actively activate for intros, expertise, and access.
Lesson 4: Etiquette Still Decides Who Gets Funded
A recurring theme of the night was how small the venture world really is, closer to a small town than an anonymous marketplace. Derrick described sitting in a New York happy hour where nearly everyone in the room had already seen the same AI startup’s deck, several from the same meeting. Reputation travels fast, which makes straightforwardness, even when the answer is no, more valuable than overselling.
Both panelists pushed back on a few habits founders should drop entirely. Don’t pitch in the hallway at a conference: deals never actually close in that setting, it just makes an otherwise organic, human connection feel transactional and awkward. The better move, Damian said, is to have a normal conversation, connect afterward, and let the follow-up be the pitch.
Don’t demo on your phone unprompted, either. Jane chimed in and shared what might be the night’s most memorable story: an investor at a previous Outside In event was followed into a bathroom by a founder pitching through the stall door, and, unsurprisingly, it did not lead to a check.
And stop leaning entirely on AI to generate your deck. Derrick relayed blunt feedback from an investor friend who reviewed a fully AI-generated deck and called it “AI psychosis slop,” a phrase that got a laugh, but landed the point that investors can tell.
Lesson 5: Traction Beats Ideas at Pre-Seed
Asked what a pre-seed founder should prioritize with limited time, Damian’s answer was consistent: find one design partner or early customer and build around them. While some pre-seed funds will still fund at the idea stage, Level Up, like a growing number of early-stage funds, wants to see product and revenue signals, even small ones. Three to five paying or committed customers, he said, is often enough to make a pre-seed round meaningfully easier to close, because it shows the founder can sell, not just build.
Market size still matters enormously, even at the earliest stages. Funds want to back big, non-obvious ideas with real scale potential, and Damian cited an example of a prominent fund backing a company built around AI agents that could themselves become founders, despite having no traditional product at the time of investment.
Derrick added a sharper framing: a good idea is not the same thing as a good business, and pre-seed funds are increasingly requiring some evidence of early traction or a real sales pipeline before writing a check, because without it, founders often stall out permanently at the seed stage with no way to raise further.
Lesson 6: Founders Control More of the Process Than They Think
The evening closed with audience questions that pulled in some of the most tactical advice of the night.
On crowdfunding, Damian was candid about the tradeoffs. It demands serious marketing skill, since success depends on a compelling public campaign, and it comes with real downstream complexity: potentially hundreds of small, unaccredited investors, each expecting outsized communication relative to their check size. He pointed to platforms like StartEngine, WeFunder, and Kickstarter, but Derrick offered a sharp warning from the legal side: crowdfunding platforms themselves can shut down, leaving founders with unmanageable cap tables, sometimes 150-plus line items, that become expensive to unwind later. His alternative for smaller, friends-and-family-style raises is to use a platform like Sidecar to set up a special purpose vehicle, which consolidates many small investors into a single cap table line item and keeps the data room clean for future diligence.
On finding the right investors to target, both panelists pointed to the same core tactic: ask a prospective lead investor to connect you with founders already in their portfolio, then ask those founders directly how engaged and helpful that investor actually was post-check. Founders tend to be candid with each other in a way that avoids the usual sales gloss. Damian added a more modern research technique of his own: using tools like Claude and Gemini to scrape investor bios, published writing, and social presence to build a targeted list of the right investors for a specific thesis, rather than blasting cold outreach broadly.
And on data room hygiene, Derrick was emphatic that it’s one of the few things entirely within a founder’s control, and clean data room habits pay off directly in speed and trust during diligence. A messy, document-dump data room doesn’t read as “we have a long history.” It reads as disorganized, and it actively slows down an investor who was already leaning toward yes.
The Takeaway for Founders
Strip away the specific mechanics, the deck formatting, the SPV structuring, the LinkedIn cadence, and the through-line of the night was consistent: venture capital, especially at the earliest stages, still runs on human relationships, not just spreadsheets. The founders who stand out aren’t necessarily the ones with the flashiest pitch. They’re the ones who show up prepared, communicate honestly when things change, treat investors as long-term partners rather than one-time transactions, and understand that the fundraising process never really stops. It just gets easier when the relationships are already in place.
Frequently Asked Questions
What is Level Up Ventures? Level Up Ventures is the pre-seed and seed-stage venture fund backed by Hearst, focused on founders who have historically had less access to capital. It typically writes checks of $300,000 to $500,000 across fintech, sustainability, sports and media, healthcare, and supply chain and logistics.
What does a pre-seed investor look for besides the pitch deck? Beyond a clear, well-organized deck, investors like Level Up look for consistency between what a founder says in different meetings, an active and visible online presence, and early traction, such as three to five paying or committed customers, even at the idea stage.
What should founders avoid when approaching investors? Avoid pitching in hallways at conferences, demoing unprompted, sending repeated unsolicited messages, and relying entirely on AI to generate a pitch deck. Investors talk to each other, and reputations travel fast in a small ecosystem.
How should founders work with investors after closing a round? Treat investors as active team members rather than passive check-writers. The strongest founder-investor relationships involve regular updates, specific requests for intros or customer help, and using an investor’s resources and network well beyond the initial check.
Are SPVs a better option than crowdfunding for smaller raises? For friends-and-family-style raises, a special purpose vehicle can consolidate many small investors into a single cap table line item, which keeps the data room cleaner than a crowdfunding campaign that can leave founders managing hundreds of small, unaccredited investors.
By: Gretchen Weaver & Dwayne Tabb, Innovation Works
Thank you to our Outside In sponsors: Buchanan Ingersoll & Rooney, Faros, and Fox Rothschild.