Gig to Grow Business Summit 2026
From Start-Up to Sc
A practical, high-energy business summit Toronto 2026 for entrepreneurs, small business owners, and growth-minded professionals ready to grow smarter, connect deeper, and take their next bold business step.
Come for the insight. Stay for the connections. Leave with momentum.
For entrepreneurs, business owners, side-hustlers, service providers, and professionals ready for their next level of growth.
Sylvia Calleri
Event Co-Host & Speaker
Laura Connor
Event Co-Host & Speaker
Roger Caesar
Event Emcee
Dr. Jude Joseph
Featured Speaker
Nadine Zeinoun Khoury
Featured Speaker
Winston Stewart
Keynote Speaker
Jady Nugent
Featured Panelist
Alan Luk
Featured Panelist
Chantel Escoffery
Featured Panelist
Judy Stewart
Featured Panelist
Rina Winston
Featured Panelist
Zehra Mahoon
Featured Speaker
Bill Hutton
Featured Panelist
Edith Taki
Expert Coach
Lisa Watts
Expert Coach
Kat Ostroumova
Expert Coach
Sylvia Calleri
Event Co-Host & Speaker
Laura Connor
Event Co-Host & Speaker
Roger Caesar
Event Emcee
Dr. Jude Joseph
Featured Speaker
Nadine Zeinoun Khoury
Featured Speaker
Winston Stewart
Keynote Speaker
Jady Nugent
Featured Panelist
Alan Luk
Featured Panelist
Chantel Escoffery
Featured Panelist
Judy Stewart
Featured Panelist
Rina Winston
Featured Panelist
Zehra Mahoon
Featured Speaker
Bill Hutton
Featured Panelist
Edith Taki
Expert Coach
Lisa Watts
Expert Coach
Kat Ostroumova
Expert Coach
Is This Small Business Growth Summit for You?
This summit in Markham Ontario is designed for:
Small Business Owners
You are already building and want sharper strategies, stronger support, and better growth opportunities.
Start-Up Founders
You are creating something new and want to build with clarity instead of guessing your way through every step.
Side-Hustlers Ready to Grow
You have been treating your business like a side thing, but you know it is time to get serious.
Service-Based Entrepreneurs
You sell your skills, expertise, or services and want better visibility, systems, and client attraction.
Coaches & Creatives
You are ready to position your value, connect with the right people, and grow with more confidence.
Established Builders
You have been in business for a few years and are ready to move from survival mode to scale-up thinking.
Growth-Minded Pros
You value learning, networking, personal development, and being in rooms that stretch your thinking.
Community Connectors
You believe business grows better when people share resources, relationships, and opportunities.
You do not need to have it all figured out.
You just need to be ready for your next step.
This Is Not Just Another Business Event
You started the business.
Now you are ready for the next level.
The Gig to Grow Business Summit: From Start-Up to Scale-Up was created for entrepreneurs who want practical insight, real conversations, and access to people who can help them grow at our entrepreneur conference Ontario.
This is for the business owner who has the vision, the talent, and the drive, but knows it is time for better systems, stronger visibility, smarter tools, and deeper connections.
No fluff. No boring conference energy. No sitting in a room wondering, "Okay… now what?"
This startup to scale up event is built to help you learn, connect, take action, and leave with momentum. Get your entrepreneur event tickets today.
What to Expect at Gig to Grow Business Summit
Powerful Speaker Lineup
Hear from business leaders, experts, and entrepreneurs sharing practical insight on growth, visibility, technology, leadership, and building a business that can last.
Expert Panels
Listen in on honest, useful conversations about what it really takes to move from start-up energy to scale-up action.
Coaches Corner
Get access to practical support from six secured business coaches and experts who can help you think through your next move.
Scale-Up Marketplace
Meet vendors, explore business tools, visit partner activations, discover resources, and connect with organizations that support entrepreneur growth.
Natural Networking
Connect with entrepreneurs, service providers, partners, and community leaders in a room designed for real conversation.
Actionable Resources
Leave with ideas, tools, contacts, and next steps that can help you move forward after the summit ends.
Meet the Voices Helping You Grow
Our speaker lineup is already coming together, and this year's summit is focused on practical insight that entrepreneurs can actually use.
Expect real-world conversations around business growth, AI and technology, visibility, leadership, marketing, funding readiness, systems, and the mindset needed to move into your next level.
These are not just talks for the sake of talks. Meet our business summit speakers and get ready to be inspired.
The goal is for you to leave saying:
- "I needed that."
- "I can use that."
- "I know what step to take next."
Step Into the Coaches Corner
Sometimes you do not need another 90-minute lecture. Sometimes you need someone to look at your business and help you see the next step more clearly.
That is what the Coaches Corner is designed to do.
This year, we have secured some amazing coaches and experts who will bring practical guidance, business insight, and real support to attendees.
Whether you need help thinking through your marketing, messaging, systems, visibility, funding readiness, business planning, or next-stage growth, the Coaches Corner gives you a chance to get closer to the kind of support many entrepreneurs usually have to search for on their own.
Built on Real Momentum
Our first Gig to Grow event proved something important: Entrepreneurs are hungry for practical learning, meaningful connection, and rooms where they feel seen, supported, and challenged to grow.
The feedback was phenomenal, and this year we are building on that momentum with a stronger experience, more intentional partnerships, and even more opportunities to connect.
"Honesty everything was fantastic - great topics, speakers, vendors - you hit on all the important topics for people to think about if they were starting their business but even for those who are a few years in and growing. And Emcee was fantastic, engaging and FULL of energy. It was such a fantastic day."
— Charlotte K.
"Well organized, a lot of information was shared on a high level, connecting with other business owners and it was fun!"
— Carol W.
"Incredible day and so blessed to be a part of it! So many great takeaways and such a genuine way to build communtiy with like-minded and supportive individuals! Excited for what’s in store for me as I grow my brand and services and can’t wait to share my glow up success story at next years event! Let’s GO!!"
— Adam K.
Your Summit Day May Include
This is a full-day experience created to help you learn, connect, and grow.
Ready to Move From Start-Up to Scale-Up?
If you are building something, growing something, or supporting the people who do, this summit was created with you in mind.
Gig to Grow Business Summit: where business growth gets practical.