Agenda: May 14, 2026
Two tracks. Eleven masterclass sessions. One day built around where your business is right now. Choose your path, or mix and match.
Build the Foundation: designed for solos establishing the systems, strategy, and financial footing to grow with confidence.
Grow to the Summit: built for solos ready to scale what's working and push their business even further.
Professional Creators
You make the content. We run your back office.
Keep more of what you earn with Lettuce. We’ll set up your S Corp to handle payroll, bookkeeping, tax filing, and healthcare benefits so you can save money and stay focused on your brand.
Why creators love Lettuce
“I’m great at what I do, but financially and business‑wise I was a disaster. Lettuce separated my personal and business finances, put everything on rails, and took this huge weight off my shoulders.”
Rebecca Firth, Food Blogger & Cookbook Author at Displaced Housewife
“Where Lettuce has been particularly helpful is in making sense of my taxes and organizing the chaos, because I’m not an accountant. I don’t know enough about it on my own.”
Ryan Welton, Local Media Creatorat Oklahoma Memo
“Where Lettuce has been particularly helpful is in making sense of my taxes and organizing the chaos, because I’m not an accountant. I don’t know enough about it on my own."
Ryan Welton, Founder at Doable Digital Media
8:30am PST
Keynote
How to Change Anyone's Mind
Everyone has something they want to change. Solopreneurs want to close the deal. Consultants want to shift a client's thinking. Fractionals need to drive alignment across teams they don't fully control. But change is hard. We persuade and cajole and push and push, but even after all that work, often nothing happens. Things change at a glacial pace, if at all. Could there be a better way?
This talk outlines a revolutionary approach to change. Successful change isn't about pushing harder or exerting more energy. It's about removing barriers. Overcoming resistance by reducing friction and lowering the hurdles to action. Discover the hidden factors that impede change, why your biggest competitor is inertia, and why big changes require asking for less, not pushing for more. Whether you're trying to win over a skeptical prospect, get buy-in from a client's internal team, or move a relationship from conversation to contract, this talk will teach you how to become a catalyst..
8:45am (PST) / 11:45pm (EST)
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Jonah Berger Wharton School professor, author of Magic Words, Contagious, Invisible Influence, and The Catalyst. |
10am PST
Build
Build Your Business the Right Way (So You Don’t Have to Fix It Later)
The real issues for solopreneurs usually don't show up right away. They come from early decisions that didn't seem like a big deal at the time but compound later. Diane Kennedy, CPA and tax strategist, walks through the core financial foundations every solo needs: how to think about income, expenses, and structure, and the common mistakes that lead to missed deductions, cash flow stress, and unnecessary taxes. You leave with a clearer picture of where you stand and what to fix first.
10:00am (PST) / 1:00pm (EST)
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Diane Kennedy CPA, Strategic Tax Consultant, US Tax Aid |
Grow
Stop Leaving Money on the Table
The tax code has built-in advantages for solo business owners. Ankur Nagpal walks through the moves that actually move the needle: entity structure, estimated payments, retirement accounts, and the S-Corp decision that high-earning solos can't afford to get wrong. You leave knowing exactly where you stand and what to do next.
10:00 am (PST) / 1:00 pm (EST)
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Ankur Nagpal Founder, Carry and Silly Money |
10:45am PST
Build
Claim Your Narrative and Become the Obvious Choice
Solopreneurs undersell themselves not because they lack expertise, but because they haven't found the story that makes that expertise stick. Renee guides attendees through building their personal narrative from the ground up: the through-line that connects who you are, what you do, and why the right clients choose you. You leave with a written positioning statement, ready to use.
10:45 am (PST) / 1:45 pm (EST)
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Renee Frojo Brand Storyteller & Content Strategist, A Good Reputation |
Grow
Toss Out the Algorithm Fads: Elevate Your Visual Content Without the Cringe
Most solos know their LinkedIn visual game isn't working. Few know why. Wes will provide an AI critique tool that attendees can run on their own LinkedIn visuals in real time, share the framework behind what actually attracts conversations, and do live teardowns of real examples from the wild. This is a direct evolution of his Summit 1 session — moving from the 'Why' of expertise visualization to the 'How'.
10:45 am (PST) / 1:45 pm (EST)
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Wes Wheless Founder, Positioning and IP Capture for Solo Consultants |
11:30am PST
Break (15min)
11:45am PST
Build
Get the Daily Grind Out of Your Head
Busy and productive are not the same thing. Attendees map their current week against a simple framework: what requires your judgment, what requires your time but not your thinking, and what shouldn't exist at all. You leave with a prioritized list of what to automate, delegate, or eliminate in the next 30 days and real instruction on how to execute.
11:45 pm (PST) / 2:45 pm (EST)
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Joe Casabona Founder and Podcast Host, Simple Systems for Solopreneurs |
Grow
Stop Getting Ghosted by Turning Your B2B Proposals Into Contracts
You finished the discovery call feeling good. You spent hours on the proposal. You hit send, and then nothing. Sales consultant Allison Davis introduces the one thing missing from most B2B consultants' sales process: the Fingerprints Meeting, a deliberate touchpoint between discovery and proposal that changes everything. You leave with a Fingerprints Meeting outline, sample scripting, and question bank ready to use.
11:45 pm (PST) / 2:45 pm (EST)
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Allison Davis Sales Consultant & Trainer, Sales Done Differently |
12:30pm PST
Break (15min)
12:45pm PST
Build
Turn What You Know Into What You Sell
The gap between having a skill and getting paid for it consistently is where solo businesses get stuck. Luke Kim walks through his solo founder framework, covering Founder-Market Fit, Founder-Problem Fit, and how to become your own cash cow without raising capital or hiring a team. This is practice over theory: rapid cycles, no one-trick ponies, and multiple income streams built from what you already know. You leave knowing exactly how to turn your expertise into a profitable offer and what to do in the next 30 days to get there.
12:45 pm (PST) / 3:45 pm (EST)
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Luke Kim Solopreneur Course Creator & Founder, Truth Cartel, UC Berkeley, Times of India |
Grow
Seek the Overlap: How to Find the Right Partners for Your Business
The challenge in networking isn't meeting more people. It's activating the relationships you already have. Bailey Hancock shares her Overlap Method to help attendees identify aligned partners, build relationships rooted in reciprocity, and create real opportunities through connection. You leave with a simple framework for evaluating potential partners and making more intentional decisions about where to invest your time.
12:45 pm (PST) / 3:45 pm (EST)
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Baily Hancock Connection Strategist, Overlap Collective |
1:30pm PST
Vibe Coding Session
What Solos Can Build With AI Right Now
You don't need a technical background to build custom websites, virtual assistants or client-ready proposals for your business anymore. Dan Sears and Garrett Kelly show what's now possible for solos in a fast, hands-on 30-minute session: real projects, real tools, and a clear starting point so you leave knowing exactly what to build next and where to go to learn more.
1:30pm (PST) / 4:30pm (EST)
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Garrett Kelly Head of Operations, EmberAI |
2pm PST
Closing
Stop Waiting to Be Picked: Claiming Your Power and Profits as a Solopreneur
In this empowering keynote, Lindsay MacMillan challenges you to stop waiting for permission and start choosing yourself as a solopreneur. Drawing from her journey from Wall Street VP to bestselling author, speaker, and creative entrepreneur, she shares what it really takes to build a business, brand, and body of work on your own terms.
You'll learn how to position yourself as the opportunity, move through rejection without losing your voice, and take bold, aligned action. Through storytelling, mindset shifts, and practical tools, Lindsay shows how to turn your ideas and skills into real revenue and meaningful impact without waiting for gatekeepers to pick you.
This session is designed to ignite you and inspire you. You'll identify where you are currently giving your power away, name what would shift if you stopped waiting to be chosen, and commit to one micro action you will take to reclaim your power.
You'll leave this talk feeling lit up and ready to carry the energy of the summit forward and step into your next level as a solopreneur.
2:00pm (PST) / 5:00pm (EST)
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Lindsay MacMillan Author, Lindsay MacMillan Creative |