Ladies Open Air Society
Co-Founder
I wanted to make friends with ladies who like to be outside...so I co-founded and run monthly outdoor-ish gatherings for ladies. We make friends, get outside, and get back to nature.
Rianna Lettini
Operations & Systems Consultant for Early-Stage Founders
New York, United States (-05:00 UTC)from New York, United States
Usually responds in 2 hours
Free
Price per hour
30 min
Time Blocks Available
5.00
2 reviews / 2 sessions
Fri
09
Next availability
Bio
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.
Expertise
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.
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.
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.
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.
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.
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.
Experience
Rosettini
Founder & Decision PartnerRosettini is my love letter to every founder who can't sleep and feels like they're on a runaway train watching the world go on without them. Trite but true: your business is your baby. And just like a human baby, it can be loud, chaotic, completely derail your entire day, and still be the most rewarding experience of your life. Maybe unless you have actual human children? I wouldn't know, I'm a dog mom! At Rosettini, I work 1:1 with founders to reduce some of that loud chaos so you can focus on the rewarding part. So your days can be more predictable and proactive instead of just responding to whatever came up that morning. Some of what that work looks like in real life: ✧ A safe space to think out loud ✧ Deciding what's actually important versus what just feels urgent ✧ Learning delegation, and unlearning some of your perfectionism ✧ Hiring: who, when, and whether you need to at all ✧ Employment structure: contractors, employees, policies, and the legal side you probably didn't even know about ✧ Org design and knowledge retention, so you can actually train someone new If any of that sounds like your week, my intro calls are free. Send me a message! If none of this resonates, please reach out and share your secrets! It's pronounced Rose-tini - a mashup of Rose and Lettini <3
Dusted
FounderDusted was an online specialty grocer focused on stovetop popcorn goods. I ran it solo from my Greenpoint apartment, and was very happy to offload my extra inventory after closing. Some things I learned: ✧ Starting a business is hard. ✧ Running one is harder. ✧ Deciding to close one is hardest. ✧ Growth Sucks (if you aren't in pain, are you even learning anything?) ✧ The day-to-day really matters, and no two businesses have the same one. ✧ Knowing what you're good at is helpful. Knowing what you're bad at is imperative. ✧ Meta sucks. ✧ A surprising number of people want money from you that you clearly do not have.
Near Space Labs
Head Of Operations✧ Brought in to stabilize and unify operations across a scaling distributed aerospace team. Owned HR, finance, compliance, and KPIs. ✧ Designed and implemented a new performance system that decoupled reviews from compensation, aligning pay to company health and market benchmarks, while freeing performance reviews to focus on performance. ✧ Acted as connective tissue across the org, building cross-functional workflows and internal rituals.
Mint House
Director Of Operations✧ Diagnosed and repaired operational vulnerabilities during a period of aggressive growth: redesigned the BizDev-to-Expansion pipeline, rewrote internal policies across departments, and overhauled the insurance program to reduce risk portfolio-wide. ✧ Acted as internal consultant to the C-suite, bridging the gap between leadership strategy and operational execution. Balanced institutional knowledge with strategic change, improving corporate resilience and cohesion. Mint House was acquired by Kasa in 2026
Mint House
Operations Manager✧ Scaled the company from one market to many by building remote ops infrastructure—hiring and managing local teams, vendors, and workflows across cities. ✧ Led expansion logistics for building launches, improving coordination and shaving weeks off the timeline from contract execution to revenue recognition. ✧ Built and led the guest experience function from scratch, integrating real-time feedback to improve both baseline service and “surprise and delight” moments. ✧ Drove cross-functional initiatives like GDS onboarding, serving as a systems-focused source of truth across ops, product, and customer-facing teams.
1776
Campus Manager, 1776 NYC✧ Brought on to open and operate a new 6,000 sqft tech campus for 100+ startups. ✧ Handled construction punch-lists, member management & onboarding, sales targets, market research, vendors & facilities, and daily ops from the ground up. 1776NYC campus was closed in 2017 after 1776 merged with Benjamin's Desk.
MoLabs Inc.
Office & Operations Manager✧ Joined as the first and only operations hire. Owned HR, onboarding, vendor management, facilities, and finance. MoLabs was acquired by Snapchat in 2016.
Grand Central Tech
Operations Manager at Build Grand Central✧ Launched a 40k sqft co-working hub from blueprint to full occupancy of 250+ seats. Managed facilities, billing, security, and member experience. Build at Grand Central Tech was the co-coworking space associated with GCT, now known as Company Ventures and is now part of the ecosystem 22 Vanderbilt.
CARROT
Executive Assistant to CEO✧ Originally hired to support the CEO during a period of rapid growth; quickly became a trusted operator across internal strategy, investor relations, and special projects. ✧ Built onboarding programs and team culture initiatives that helped scale the org from 12 to 60+.
CARROT
Partner✧ Shaped strategy, M&A diligence, and the successful acquisition by VICE in 2013.