Rianna Lettini

I've spent 15+ years deeply embedded in startups in various industries. Usually as an early employee (like #2), and later as a founder myself, meaning I've done a little (lotta) bit of everything. Guest experience, running a hotel remotely, paying the bills, reviewing contracts, building teams, often in the same day. That range gives me the unique perspective of seeing how the entire organization fits together and how decisions now unfold in the years to come. I can usually hear where something isn't lining up in a business, even when I'm not the one who built it in the first place. These days I consult with early-stage founders on the internal side of the company. Most of my work is in knowledge retention and operational improvements: getting what lives in your head written down, clarifying who owns what, cleaning up handoffs, and working out what you can hand off so you can do your actual job. Fun fact: I have a terrible memory, which is exactly why I got good at building systems that don't rely on anyone "just remembering to do it". I got a taste of the founder experience when I launched my own specialty grocery (yes, that was a pun, gotta find your own joy in this world!). Those two years were a real crash course that gave me an entirely new understanding of the previous years of my career. One of the hardest decisions was choosing to shut it down after only 2 years. I loved the concept, but to be blunt, I hadn't really validated my market nor the day to day experience of building that particular business. Let me share my experiences so you don't have to repeat my mistakes. Book me if: - You're a first-time founder at an inflection point and the things that used to work have stopped working - You're doing everything yourself and need to figure out what to delegate, and how - Your team is unclear on who owns what, or knowledge keeps walking out the door - You want to think out loud with someone who'll turn it into operational next steps (what to build now, what can wait) Where I'm not your person: go-to-market, marketing, and audience validation aren't my skill set. If that's where you are, I'll find the right person to point you to.

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  Bootstrapping

  I started my own company a couple of years ago, a full left turn from the 14 years before it, and closed it after two years. I learned more from that than from almost anything else: what I hadn't validated, what the day to day was really going to be, and when to stop putting money and time into something. If you're deciding whether to keep going, change direction, or wind something down, I'm happy to be the person who asks the uncomfortable questions.

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  Building a team

  I've been the early employee doing guest experience, running a hotel remotely, and reviewing contracts in the same day, so I know what it looks like when everything sits on too few people. I can help you work out what to delegate first, who should own what, and how to hand something off so it doesn't come straight back to you. Happy to get into the awkward parts too: setting expectations, communicating change, and documenting so a departure doesn't take the knowledge with it.

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  Career guidance

  I made a full career pivot after 14 years, ran it for two years, then chose to close it, so I have a lot of sympathy for anyone weighing a jump. Some of the work I'm proudest of is talking friends out of businesses they didn't actually want to run. One was torn between a logistically heavy fashion brand and selling sourdough. A few questions about funding, margins, and what her week would actually look like made it obvious. She now runs a thriving farmers market sourdough business.

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  Leadership

  Most first-time founders start a business because they're good at the thing, not because they wanted to manage people or write a mission. Then the company grows and those become the job. I work with founders at exactly that inflection point, when the way you've been operating stops working and you're not sure what to change first. Expect questions about how you actually spend your week, what you keep avoiding, and what genuinely only you can do.

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  Operations

  This is the core of my work. I help founders see how their business actually runs day to day, then clean up what creates drag: unclear ownership, messy handoffs, and work that lives only in someone's head. I start with knowledge loss, because that's what quietly breaks as you grow. I care as much about implementation as design, so we'll talk about what changes on Monday, not just how the process should look on paper.

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  Venting frustration

  Clients have called me a founder therapist and I've grown to like it. Sometimes you need to say the whole mess out loud to someone who isn't inside it with you. I'll listen, tell you what I'm actually hearing, and then turn it into something you can act on, along the lines of "you don't need a new tool here, you need a bookkeeper." No judgment about how tangled things have gotten. I've been in it too.