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.

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Why creators love Lettuce

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“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

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“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

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“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

 
Welcome & Keynote

 

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)

Ankur Nagpal

 

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)

wes_Wheless

 

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)

Allison Davis

 

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

Don't forget to register!