If you’ve spent years operating inside companies—shipping product, building go-to-market, wrangling budgets—you already have an asset most early-stage founders would love to borrow: your hard-earned pattern recognition. In a recent salon, longtime enterprise technology leader Abby Kearns (former CEO of Cloud Foundry Foundation; former CTO at Puppet and Alembic) unpacked how she turned that operating experience into a flywheel of advisory work, angel investing, and board service—and how you can, too, no matter your domain.
This isn’t a story about chasing titles. It’s about staying close to the frontier of your craft, compounding your learning, and putting yourself in the rooms where opportunity circulates. As Abby puts it, she sees angel investing as “an investment in my education”—and the rest of her portfolio flows from that mindset.
From Operator to Ecosystem Player
Abby has spent 25+ years in enterprise infrastructure—dev tools, automation, security. About a decade ago, she started advising startups in that lane, giving product feedback to founders. That naturally led to writing early checks in the same companies she already knew well.
Why do both? Because the tight loop between advising, investing, and operating keeps her learning edge sharp. She brings what she’s seeing in the market back into her executive roles—and vice versa. It’s a “virtuous cycle,” she says, that keeps her relevant, plugged in, and valuable to founders and boards.
Two principles power that loop:
- Focus where you’re truly an expert. Abby’s investment thesis is intentionally narrow: enterprise infrastructure and go-to-market. “I provide zero value to companies on the consumer tech side,” she admits. That clarity helps her say no fast and go deep where she can add leverage.
- Treat it as education first, not a payday. Early checks may never return capital. But the learning, access, and deal flow are immediate. “I would like to make money off of some of these, but I probably won’t.” That mindset turns risk into tuition—and lowers the emotional stakes.
This Works Beyond Tech Infra
Maybe your world is HR, marketing, sales, med-tech, supply chain, or consumer products. The same pattern applies. Every function has a growing startup ecosystem (think HR tech, martech, revenue tech, fintech embedded in your industry). Your domain expertise makes you a scarce resource to early teams.
Your playbook starts with two questions:
- What do I bring to the table? Be specific about your value prop: Is it product-market fit intuition? Enterprise sales architecture? Pricing and packaging? Category creation? PLG motion? Talent strategy post-Series A?
- Where do I show up? Identify the hubs near you (yes, even outside the Bay Area—nearly every region has a venture node). Then go: demo days, small conferences, operator collectives, investor breakfasts, founder dinners, and firm-hosted salons. You learn in public, and you meet the people doing the next interesting thing.
“Networking, Networking, Networking” (The Non-Gross Kind)
Abby’s path is relentlessly relationship-driven. Every company she invested in came through her network—VCs who trust her judgment, founders she’s helped, operators who trade deal notes. That network isn’t built on slick intros; it’s built on recency and reliability:
- Show up consistently. VCs “forget,” Abby says. Staying visible creates helpful recency bias. If you were the smart, candid voice they heard last week, you’re top of mind when a founder needs help with pricing or an allocation opens.
- Do the first coffee for free. Early on, Abby took lots of exploratory meetings without compensation to learn, help, and build trust. As her time compressed, she set healthier boundaries (more on that below), but the give-first reputation stuck—and so did the inbound.
- Be direct. Founders crave an honest signal. Abby is known for clear, unsugarcoated feedback: what will and won’t work, where to focus next. That candor is a differentiator.
Advisory as a Pathway to Boards
Has writing checks put Abby on boards? No. She’s on zero boards because she invested. Board seats came through the same network, selected for specific gaps she could fill (product, enterprise GTM)—sometimes via VCs who’d watched her diligence deals or coach founders.
That distinction matters. Don’t assume a $10k check buys governance influence. Instead, prove your value in the ecosystem: diligence support for funds, advisory sprints for founders, hands-on help solving go-to-market knots. That’s what gets you recommended when a CEO or VC needs an independent director with your spike.
Deal Flow When You’re New
If you’re not already in the stream, how do you find the deals (or let them find you)?
- Angel networks. Groups like Modern Angels (women-led) and other local/sector collectives share deal flow and learning. Many are thesis-agnostic and accessible at low check sizes, with occasional SPVs for one-off deals.
- Operators-as-LPs funds. Abby is an LP in Operator Collective (women operators pooling small LP checks to back founders, with strong introductions both ways) and two infra-themed funds (Aviso and Essence). Being an LP spreads risk and puts you on the update list for every portfolio company—plus warm intros.
- VC relationships in your lane. Identify firms whose theses match your expertise. Offer targeted advisory time to their founders. Funds love adding high-leverage operators around a portfolio CEO—and often have allocation carve-outs for trusted angels when rounds close.
- Local hubs and firm events. Even outside major tech centers, regional hubs host pitch nights and portfolio showcases. Go. Ask questions. Offer a follow-up session. “Show up” is unglamorous advice—and it works.
How to Be a Great Advisor (and Not Get Overrun)
Early on, Abby did a lot for free—30 to 60-minute feedback sessions, crisis calls, and tactical help. That generosity quickly built her reputation. Over time, she introduced a reasonable structure. She maintained access but with boundaries: if the relationship became ongoing, she would formalize it with clear scope, cadence, and compensation. Abby also calibrated her involvement to each founder’s needs. Some wanted weekly check-ins, while others might disappear for a year, and she learned to match her level of engagement to the moment. Her role was to be the no-BS truth serum; founders already received plenty of polite noise from boards and investors, so her value lay in being specific, honest, and actionable. She also came to expect that she’d hear from them mostly when things were hard. When everything was going well, there might be silence—and that was normal. She remained the steady voice on the other end of the line when they called at 10 p.m.
Equity, Cash, and What’s “Normal” for Advisors
Comp depends on stage, time, and depth:
- Equity: For “pretty aggressive” advisory (think 1–2 hours/week, hands-on problem solving), ~1.0% isn’t unheard of at very early stages. For deep-tech with long time horizons, ask for more or blend equity + cash.
- Cash: It is not a red flag for a founder to include modest cash advisory budgets in a seed/Series A use of funds. VCs generally praise founders who surround themselves with help early.
- Boundaries: Don’t let quick advice turn into an unpaid part-time job. Once you cross a cadence, formalize.
LP Routes: Efficient Diversification and Access
If active angeling is too time-intensive right now, consider LP roles in funds aligned to your thesis. Benefits:
- Diversification: One commitment spreads across a portfolio.
- Passive learning: Quarterly updates = ongoing market education.
- Warm intros: Ask funds for founder introductions where you can help.
- Community: Operator-focused funds (e.g., Operator Collective) intentionally connect founders to domain experts—that’s you.
Other communities like Portfolia (member-involved diligence and pitch access) give you a front-row seat to how investors evaluate teams and markets, plus opportunities to participate as an LP.
Women, Risk, and Buying Your Way Into the Room
The salon conversation surfaced a point many of us recognize: men have long “played” the early-check game, writing $10k checks for years—and compounding the network, education, and, yes, wealth that accrue. Women are often rewarded for prudence, which can calcify into over-conservatism. Abby’s reframing helps: call it tuition. Spend what you can truly afford to learn. And remember: writing a check sometimes buys your way into conversations you might not otherwise enter. That exposure alone can shape your next executive role, advisory portfolio, or board seat.
Practical Next Steps
- Write your thesis on one page. Problem spaces you know cold; stages you prefer (pre-seed/seed); how you help (e.g., “Enterprise GTM architecture; pricing & packaging; recruiting first 5 sellers; PMF diagnostics”). This is your filter.
- Map the local and virtual hubs. List 5 funds in your thesis, 3 operator/angel communities (e.g., Modern Angels, Portfolia syndicates), and 3 recurring events you can attend. Put them on your calendar.
- Offer two “office hours” blocks a month. Invite VCs/founders in your lane to book 30-minute sessions. You’re building reps and reputation.
- Shadow a diligence. Ask a friendly VC or LP community if you can sit in on one diligence. You’ll learn how investors interrogate a market—and where your operator lens adds signal.
- Decide your tuition band. Pick a comfort-not-panic number for angel checks (or an LP amount) and stick to it for your first 1–3 investments.
- Create your advisory boundary script. “Happy to do a first meeting and one follow-up. If ongoing support would help, here are two ways we could structure it…”
- Follow up like clockwork. After events or calls, send crisp notes: what you heard, two tactical suggestions, and one intro you’ll make. Be the person who closes loops.
The Long Game
Abby’s portfolio didn’t emerge from a grand plan; it grew from curiosity, consistency, and clear edges. She shows up. She knows exactly where she’s valuable. She stays close to founders and investors, solving the problems she loves. And she’s comfortable with the ambiguity and risk that come with private markets, advisory equity, and long time horizons.
You don’t need to live in Silicon Valley to play this game. You don’t even need to start with a check. Start with your thesis. Start with a coffee. Start by showing up.
Because the compounding effects—education, access, influence, optionality—favor the operators who lean in, tell the truth, and keep the flywheel spinning.
