The only question the investor is really asking
She raised millions, failed, and now writes the checks. Here's what she looks for.
Every room where something big gets decided is asking one question about you: can this person deliver? Investors ask it before they wire money. Boards ask it before they back a plan. Your team asks it in every hard week, even when nobody says it out loud.
Taisiya Kudashkina, Taya, has sat on both sides of that question.
She grew up in Siberia, landed in Silicon Valley with an engineering degree and almost no English, and stayed six years. In that time, she fell in love with startups and the Silicon Valley culture and ethos. Back in Russia she built four businesses, raised over two million dollars at pre-seed for one of them, and watched it fail in the same season her marriage ended. In 2022, she left the country over the war and started again in Luxembourg, where today she writes angel checks into fintech and AI startups.
Ask her what she is looking for across the table and her answer covers more than the pitch: show them you can deliver, tell the story so they can see it, and protect the person the delivering depends on.
Here are the five ways she answers that, from our conversation
1. The only question in the room: can you deliver?
At the stage where Taya invests, there is almost nothing to analyze yet. “You don’t have too much data yet... everything that you have is that founder who is in front of you, and you are trying to understand, is he able to deliver? This is pretty much the only question which an investor has.” She refers to founder-product fit: “I just want to see... if you particularly, with your skill set, with your experience, with your desire and your motivation, will be able to deliver this particular business.” Notice what is missing from that list: the polished deck or the financial model projecting the future. It’s a tough road to building a company, so investors need to believe you are the right person for that path ahead. And this question does not retire after the seed round. Swap the investor for a board, a CEO, or a leadership team, and it is the same question, asked about you, in every room you walk into.
To Coach yourself: Bring to mind the room you most need a yes from right now. If they judged nothing except your ability to deliver this specific thing, what would they see as evidence? Where are you asking them to take it on faith? What proof could you put in front of them this month?
2. Tell it so they can see it.
The fastest way to lose an investor is to be unclear. Taya sees it constantly working with university spin-offs: “Those people are so much in their research. They cannot communicate well enough. Sometimes you can’t even understand what is this product about.” The product might be years of brilliant work, and it dies in the meeting anyway: “If I cannot understand what is this about, no way you’re going to get the money out of me.” Her redemption clause matters just as much: “It’s not something we were born with. You still can learn that skill.” The skill she is referring to here is the skill for storytelling. Clarity is what conviction looks like from the other side of the table.
To Coach yourself: Take the thing you are pitching right now, a round, a budget, a change. Could a smart outsider repeat it back after hearing it once? What would you cut so the story survives one telling? Who will you test it on this week?
3. A failure does not disqualify you.
The thing that shocked her most about Silicon Valley: “You are not guilted, but you are encouraged to make mistakes... We know by pure statistics that eight out of 10 startups are gonna die, and this is not your fault.” Then the part she could hardly believe: “Sometimes the same people are fundraising [with] you,” backing a founder whose last company died. Their reasoning: “I saw that you tried... you’ve made an effort... If it didn’t happen, it’s just not your fault. Something changed, the market or whatever.” She learned the opposite lesson the hard way, carrying her own failure as a verdict during the darkest stretch of her life, when she “felt like I failed everything.” The investors worth having read effort as evidence. The verdict you write about yourself is the one that decides whether you build again.
To Coach yourself: What failure are you still carrying as a verdict on you? Separate what you actually controlled from what was outside your control. If the people watching read your effort as evidence, what would that free you to attempt next?
From Taya: “Sometimes the same people are fundraising [with] you.” The people watching how you handled a failure are deciding whether to back what you build next, so the transparency and honesty in that relationship carries a lot of weight.
4. Protect the captain. Burnout is a business risk.
Taya draws a straight line between the leader’s inner state and the company’s survival: “You are the captain of that boat. If you personally don’t feel good, if you are exhausted or burned out, no business will survive, because it’s dependent on you personally, especially at the early stages.” She also knows the standard failure mode from her own darkest season: “Our first and normal reaction would be to get numb... It’s easier just to freeze.” The unprocessed stuff does not stay neutral: “You have to accept. You have to grieve. Unless you let it go, it’s going to stay and poison you.” Emotional debt compounds like technical debt, and the captain is the one system in the company with no redundancy.
To Coach yourself: What are you currently powering through that you have never actually processed? What would real maintenance look like this quarter? Name one thing you will stop absorbing on your own this week, and decide who you will say it to.
From Taya: “You have to learn to be with yourself.” That skill is built in the quiet hours nobody sees, and every hard season after it draws on the same account.
5. Keep a reinvention fund.
When Taya rebuilt in Luxembourg, she took six months to choose her next chapter deliberately, and she is honest about what made it possible: “You need to have a privilege. If you are trying to earn money for food or feed your kids, no way you can relax and spend those three to six months reflecting on yourself.” That is exactly why she reframes the emergency fund: “You need it not just to feed yourself, but specifically for the periods like this, when you have to reframe yourself.” Careers now bend more than once, for founders after an exit or a failure and for executives after a role ends: “We will have to switch two, three times our careers throughout our lives. And you need money for this.” Her other guardrail is spread: “You have to have like two, three, at least, streams of income.” The runway buys the pause, and the pause is where the next chapter gets chosen.
To Coach yourself: How many months of reinvention could you fund today? What number would let you choose your next chapter rather than take the first exit that appears? What is one move you will make this month toward that number, or toward a second stream of income?
Resources Taya mentioned
The Diary of a CEO, Steven Bartlett’s podcast. Her pick for anyone starting out: light, interesting, and wide-ranging, including innovation topics.
The Tim Ferriss Show. Her other accessible starting point. Her rule for both: pick what genuinely interests you at the level you are at now, because “your only task is to find your passion.”
20VC (The Twenty Minute VC), Harry Stebbings’ venture capital podcast. The one she listens to now that she is deeper in, with her honest warning that it is heavy for beginners, so grow into it.
Taya’s own Substack, where she writes about early-stage investing from both sides of the table, and her LinkedIn. She invited you to follow along, and it is where you will find her thinking.
Leaving you with this question: what is the one thing you are asking people to believe you can deliver right now, and what are you doing to make it easy for them to see it? Share it with me.
If anything in this article resonated with you, share it with one more person that could also use these insights.
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I’m Dar Patel, an ICF-certified executive coach (PCC), I have worked with founders and executives, and am the writer behind The Inner Game, the weekly newsletter of Little Pursuits.
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