Stop Asking for Permission: A Conversation with Helena Fogarty

Fundraising is an enigma. Most founders walk into it not knowing what to ask, how to present themselves, or whether the story even matters. And the market has only gotten noisier and harder.

Helena Fogarty has seen it from both sides of the table. She's raised capital as a founder, run a venture-backed company, and spent years in luxury strategy at places like Chanel. Now she co-founds Backable, where she helps overlooked founders actually get funded, and hosts Inside Startup Funding, where she pulls the real story out of founders who just closed a round. Her core reframe, the thing she says most founders get wrong, is that they approach raising like they're asking for permission. They shouldn't be.

You have to earn the attention

Strip away the theatrics and, Helena says, fundraising comes down to one thing: you have to earn an investor's attention, and keep it, to get the investment. There are three ways to earn it. Connections, where someone vouches for you and tells an investor they have to take this meeting. Traction, which proves people actually want what you're building, that it's a pain pill and not a vitamin. And history, which is who you are and what you've built before.

Her advice is to figure out which of the three is your strongest signal and lead with it. She works with a second-time founder who had a $90 million exit, and the team kept wanting to leave it out. Her response: no, you lead with that, because anyone who hears it takes the meeting.

Connections can be built from anywhere

Helena is honest about the part nobody likes to say out loud. If you're a white guy from Stanford who failed a few times, you'll probably still get the $20 million. Connections and resources compound, and it's not just money. It's that everything is a call or two away: the head of partnerships you need, the expert who's done this before, the friend who'll drop $100k into your round.

But her point isn't that the game is rigged and you should quit. It's that connections can be rebuilt from anywhere. Move to a hub, meet other entrepreneurs, build real trust. She's an introvert who hates events so much that one knocks her out for a week, so she found another path entirely. She started talking about fundraising on LinkedIn, building in public, which got her a podcast, which now lets her network with people one-on-one without ever working a conference room. The lesson isn't to copy her path. It's to find the one that actually fits you.

Run a tight process

The way you dissolve the power imbalance in a fundraise, Helena says, is to run a tight process. Do as much work upfront as you can, prepare your network to generate attention, and then try to book all of your first meetings inside a two-week window. And here's the discipline most people skip: if you don't get enough meetings booked, you don't start. You wait.

Because five meetings a day for two weeks makes you show up completely differently than one meeting a month. She's done both. The one-meeting-a-month version is "please, may I have your money, what can I do to get you on my cap table." The packed version is "great to meet you, Steve, I've got another meeting in ten minutes, so I've got to go." That's not a mind game or a mask. It's just what's authentically true when you have options. And it lets you end every meeting the way she coaches founders to: ask "what do you think?", let them talk, and push them toward a yes or a no. If someone's just going to add you to a list of companies they mention to their partners, that's a no, and you move on.

Be direct, not deferential

A lot of what Helena fixes is tone. When a founder wants to follow up after a meeting and starts drafting paragraphs to explain themselves, she tells them: two sentences, period, done. Nobody wants to read the rest. Be direct and efficient, not because you're putting on a brusque mask, but because you're not acting like you're a lower social caste than the investor you just met.

She's careful here. Some investors reward brash confidence and eat it up, others don't, and you should never wear a persona you're uncomfortable in. But confidence, the real kind, is what lets you walk into the room and stop asking permission for anything you're doing. Your job as a founder is to remember you're evaluating them exactly as much as they're evaluating you.

The power law, and why your VC might want you to quit

Helena walked through the math that governs a lot of early-stage funds. Out of 100 investments, roughly 90 won't be winners. A handful return two or three times, which sounds fine but isn't really enough. The money gets made on the few that return 50 or 100 times. If a fund is built that way, then it is genuinely in the VC's interest to stop pouring time and resources into the companies that won't return the fund, and sometimes even to pressure those companies to shut down early and return the remaining capital.

As a business model, she says, it makes complete sense. As the founder who turns out not to be the winner, it's a brutal experience. Which is part of why she has real respect for operator-turned-investors: the ones who've built and sold companies tend to bring coaching, empathy, and foresight, instead of a 26-year-old who's never worked in a real company telling you what to do with yours while their camera's off.

Is your business even VC-backable?

Before any of the tactics matter, Helena wants founders to answer a blunt question: are you even VC-backable? The current bar is roughly $100 million in annual recurring revenue by year four or five, and it's rising. That's very fast growth. If your honest plan is $3 million in year five, that's not a failure. It's a good business. It's just not a venture one.

She has feelings about how the phrase "lifestyle business" gets used as a slur, because a business that throws off cash you can actually live on is a wonderful thing. And there are more paths than the binary suggests: bootstrapping, seed-strapping (raise one round, get profitable, grow), or growing and taking private equity later. She bootstraps Backable on purpose. Her warning about the VC road is that you are choosing to prioritize a company, a thing that is not a living being, over your relationships, your financial health, and everything else, for the next ten years. Some people thrive in that. You should know it's the deal before you sign it.

The money's not in the bank until it's in the bank

The biggest misconception first-time raisers carry, Helena says, is that it's one and done. It's almost always far more work and takes far longer than you expect. Those "closed the round in two weeks" stories are rare, and often the clock quietly got restarted after a pivot.

Her cautionary tale is a Series A with big enterprise clients that everyone assumed was safe. Due diligence dragged, the wire dragged, prior-investor approvals dragged, and the money landed the second Friday of September on a deal everyone thought would close in July, hours before the company's bank account would have dipped below zero on payday. She's watched an investor sign a SAFE, say he wired it, and then walk away. She's watched a handshake deal and a promised Tuesday term sheet turn into a ghost. Nothing is certain until the wire clears. That said, momentum is real and it has tells: multiple investors at the table, multiple term sheets to negotiate against. The whole job is manufacturing that momentum and using it to close faster.

Relationships are the hack

I offered Helena a line I believe: people never change. Tools change, processes change, times change, but people will always get scared, get greedy, and need trust. She loved it, and finished the thought better than I did. The more automation and AI enter the picture, the more relationships and trust become the actual hack.

It shows up even in how you read rejection. VCs are drowning in outreach, much of it not even a fit, so a curt "not a fit, thanks" isn't personal. Her fix for the sting is volume: send 100 emails, not one, so a single yes feels great and the nos just become background noise. Underneath all the tactics, the thing she keeps leaning on is the oldest one. Build real relationships, earn trust, and you've got the only durable edge there is.

Key takeaways

A few things worth keeping.

Lead with your strongest signal. Investors give attention for connections, traction, or history. Find which is strongest and put it first. Don't bury the exit.

Options change everything. Book your first meetings in a two-week block and don't start until you have enough. A full calendar lets you evaluate investors instead of begging them.

Push for a yes or a no. End meetings with "what do you think?" and qualify hard. A soft maybe from someone who'll just list you is a no.

Know if you're even VC-backable. Roughly $100M ARR by year four or five is the bar. If that's not your plan, bootstrapping or PE isn't a consolation prize, it's the right fit.

Trust is the edge that lasts. The more AI and automation flatten everything, the more real relationships are the thing that actually gets rounds closed.

Frameworks worth stealing

Earn the attention, lead with your strongest signal

Investors pay attention for one of three reasons: someone they trust vouches for you, you have traction that proves demand (a pain pill, not a vitamin), or your history speaks for itself. Audit which of the three is strongest for you right now and open with it. Everything else is supporting material.

Run a tight two-week process

Do the prep, work your network, and book all your first meetings inside a two-week window. Don't start until enough are booked. Five meetings a day makes you show up as someone with options rather than someone asking permission, and options are what let you walk away from a bad-fit investor without flinching.

Push for a yes or a no

Close every meeting with "what do you think?" and let them answer. Then qualify: "What do you need to see, and if I show you that, are you in?" A vague maybe from someone who'll just mention you on a list is a no in disguise. You can only push this hard when you have other investors in play.

The VC-backable test

Before raising, check whether you fit the model at all: roughly $100 million ARR by year four or five, with the bar rising. If your real plan is a few million in year five, you don't have a failing startup, you have a good business, and bootstrapping, seed-strapping, or private equity may serve you far better than venture ever would.

Quotes worth keeping

The lines I wrote down.

You've got to earn that investor's attention, and keep it, to get the investment.

Show that it's a pain pill, not a vitamin.

The money's not in the bank until it's in the bank.

Your job at the end of every meeting is to say "what do you think?" and push them toward a yes or a no.

And the one that outlasts every tool and tactic.

The more automation, the more AI, the more relationships and trust are really the hack.

Rapid fire round

Same questions every guest. No prep, no warning. Here's how Helena handled it.

Best advice you've ever received? Something she caught recently: when people are driving you crazy, roll your eyes (ideally not visibly) and give them grace, because you don't know what they're going through. Her own addition: when you're triggered or upset, give yourself time to process before you respond.

Advice you wish you'd listened to? The people who told her that her first company wasn't VC-backable. By the time she raised, her sector had fallen out of favor and the company had been around too long, and it shut down. She wishes she'd had a plan B.

What would you tell your younger self? Buy crypto.

Ongoing challenge that keeps you up at night? Figuring out the best way for founders to raise when the rules, tools, and the way people respond are all changing faster than ever.

Favorite spot? Lola's, a restaurant on a surfing beach in Costa Rica. It's the whole reason she moved to Costa Rica for eight years.

Tool you can't live without? Claude. She tried Claude, GPT, and Perplexity side by side for a year and ended up living in Claude.

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Helena Fogarty is the co-founder of Backable, where she helps overlooked founders raise venture capital, and the host of Inside Startup Funding. A multiple-time founder, bootstrapped and venture-backed, with an NYU Stern MBA and years in luxury strategy at Chanel. Find her on LinkedIn.