Gig To Grow Summit
Where Side-Hustles Scale & Small Biz gets BIG!
Saturday, October 4, 2025
Monte Carlo Inn & Suites
7255 Warden Avenue
Markham, Ontario
(Warden Ave. & Denison St.)
Save $20 of the regular price of $199+HST by booking early!
One Powerful Day.
Real strategies, real connections, and the support you need to turn your side gig into a growing, thriving business.
What is Gig to Grow Entrepreneurial Summit?
Gig to Grow is a one-day, high-energy summit built for small business owners, solo entrepreneurs, and side hustlers who are ready to scale up. This event is your chance to learn from proven experts, ask questions, get real-time coaching, and build meaningful connections with like-minded professionals.
From using AI tools to save time & money, to growing your business with speaking, managing time better and marketing smarter, accessing funding, and handling taxes with confidence, this summit delivers the knowledge, tools, and inspiration to grow your business with clarity and support.
Let’s turn your ideas into income and your side gig into a success story.
Save $20 of the regular price of $199+HST by booking early!
Meet Your Gig To Grow Co-Hosts
Two purpose-driven women. One bold mission: to help entrepreneurs and side hustlers grow with confidence, clarity, and community.
Sylvia Calleri
Authentically Evolving
Transformational Coach, Speaker & Retreat Leader
Laura Connor
The Media Seen
AI Growth Consultant, Speaker & Trainer
Meet Our Speakers & Panelists
Roger Caesar
Caesar Empire
Leadership Expert
Debra Fraser
Caribbean HR Solutions
Global Outsourcing & Recruiting Expert
Vito Marchese
Whiteboard Studio / Constant Contact
Email Marketing Expert
Jackie Rafter
Higher Landing
Business Expert
Anita Sarda
ATJ Consulting Inc.
Entrepreneurship Transition Expert
Paul Pagliaro
Strategy Expert
Anne Bloom
Anne Bloom Coaching
Business & Leadership Expert
Jason Costanzo
Eloquium
Presentation Skills Expert
Judy Stewart
Founder, Tresolz
Marlene Marco
Founder, Heart of Networking
Charlotte Kirby
Founder, The Village Hive
Trish Tonaj
Founder, ShareYourStories.online
Karen O'Leary
Grant Specialist & SR&ED Expert
Judith Tait
Business Growth & Strategy Expert
Carol Ward
Financial Expert
Gaby Mammone
Gig To Grow Featured EMCEE
Robert Sun
Founder, Electrust Contracting, Inc.
Steve Wilkins
Franchising & Entrepreneurship Expert
Meet Our Coaches
Anna Donato
Empowerment Leadership Coach
Rina Winston
Money & Business Coach
Orzala Quddusi
Social Media Coach
Natasha Khan
Life Perspective Coach
Edith Taki
AI & Digital Transformation Coach
Lisa Pinnock
Transformational Life Coach & Writing Mentor
Lisa Watts
Website Design & Branding Coach
Featured Coach
To Be Announced Soon!
Is This Summit For You?
If you've ever said:
“I want to turn my side hustle into something real.”
“I’m great at what I do, but I need help running the business side.”
“I feel stuck, overwhelmed, or just plain tired.”
“I wish I had a mentor or community that gets it.”
“I need to grow, but I don’t know the next move.”
Then YES! Gig to Grow was made for you.
Whether you’re just starting out or already a few years in, this summit will give you the clarity, tools, and connections to move forward with confidence.
What You’ll Walk Away With
This isn’t fluff or theory—this is real-world strategy you can actually use.
Here’s just a taste of what we’ll be covering:
🧠 How to manage your time like a CEO
🤖 Which AI tools can save you hours and $$$
📱 How to promote your business without feeling burned out
🏦 Where to find grants, loans, and funding opportunities
🛡️ What you need to know about taxes, insurance, and legal
🔗 How to network with purpose and build win-win partnerships
PLUS: live coaching, expert panels, and vendors offering services you actually need.
You’ll leave with new ideas, new resources—and a plan to move forward.
Grab Your Ticket Before Prices Go Up!
Don't delay. Secure your ticket today. Commit to being in the right room for a day of game-changing growth.
Advance Tickets
Save $20 of the regular price of $199+HST by booking early!
💼 Exhibitor/Vendor Tables
We would love to have you showcase your business in our Vendor Village! For Exhibitor/Vendor information, please email [email protected] and we'll get the information right over to you.
Introducing “The Coaches Corner” – Real Coaching. Real Fast.
Need help promoting your business? Wondering how to market your next offer or get your book idea out of your head and onto the shelves? Need advice on your pricing or want a pro to peek at your website?
At Gig to Grow Entrepreneurial Summit, we’ve got a space just for that.
It’s called The Coaches Corner, and it's your chance to sit down with a coach, strategist, or expert for a free 15-minute audit or mini coaching session.
Think of it like speed dating for your business… but smarter.
Whether it’s clarity, confidence, or a good ol’ business breakthrough, you’ll find it here.
Come for the Learning, Stay for the People
You never know who you’ll meet...or how they’ll help your next big move. This summit isn’t just about taking notes, it’s about making real connections with fellow business owners, potential clients, future collaborators, and new friends who get the hustle.
📣 Come ready to connect.
📣 Come ready to be seen.
📣 Come ready to grow...with people who want to grow with you.
Ready to Grow Your Business?
No more waiting. No more wondering. This is your moment.
Gig To Grow Summit is brought to you by our amazing Partners!
Elevate Partner
Accelerator Partner
Accelerator Partner
Host Partner
LaunchPad Partner
LaunchPad Partner
LaunchPad Partner
LaunchPad Sponsor
LaunchPad Sponsor
Advance Tickets
Save $20 of the regular price of $199+HST by booking early!
Exhibitor/Vendor Tables
We would love to have you showcase your business in our Vendor Village! For vendor information, please email [email protected] and we'll get the information right over to you.
Sponsorship Opportunities
Interested in becoming a GigToGrow sponsor? Please email [email protected] and we'll get the information right over to you.
Frequently Asked Questions (FAQs)
Got Questions? We’ve Got Answers.
Who is this Summit for?
Gig to Grow Entrepreneurial Summit is designed for small business owners, side hustlers, and solo entrepreneurs who are looking to grow, scale, or structure their business better. Whether you're just getting started or have been running your business for a few years, you'll find tools, resources, and community here.
What’s included in my ticket?
Your ticket ($199+HST) includes access to all speaker sessions, panels, the Vendor Village, the Photo Room Studio, networking breaks, and the Coaches Corner (Coaching sessions are limited/first come, first serve).
What is the day's agenda?
Gig To Grow Agenda (subject to change)
🕘 8:3000 AM – Doors Open: Shop Exhibitors & Network
🎤 9:00 AM – Welcome & Intros
💡 9:15 AM – First Expert Speaker
💡 9:45 AM – Second Expert Speaker
☕ 10:15 AM – Break + Exhibitor Browsing
💡 10:45 AM – Third Expert Speaker
👥 11:15 AM – Expert Panel: Real Advice from Real Pros
🍽️ 12:00 PM – Lunch + Networking
🎯 1:00 PM – Fourth Speaker
💡 1:30 PM – Fifth Expert Speaker
🛍️ 2:00 PM – Business Owner Panel + Shopping Break
💡 3:00 PM – Sixth Expert Speaker
🚀 3:30 PM – Closing Session: Big Takeaways & Next Steps
Note: On-the-spot mini coaching sessions available throughout the day in the Coaches Corner.
Where is the event taking place?
The summit is being held in at the Monte Carlo Inn & Suites in beautiful Markham, Ontario. 7255 Warden Ave., Markham, ON L3R 1B4
What time does the event start and end?
Doors open at 8:30 AM for networking. The Summit starts at 9:00 AM and wraps at 4:00 PM.
What if I have dietary restrictions?
If you have any specify dietary needs, please email us to let us know as soon as you purchase your ticket. We’ll do our best to accommodate common restrictions like vegetarian, vegan, gluten-free, etc.
Can I become a vendor or exhibitor?
Yes! We’re accepting a limited number of vendors. If your business supports entrepreneurs (marketing, finance, tech, wellness, etc.) or if you want to showcase your business/brand, you can apply using the Vendor Registration Form
How do I become a coach in The Coaches Corner?
We’re looking for expert coaches for our "Coaches Corner". Email [email protected] to express your interest.
Is parking available?
Yes! There is plenty of free on-site parking available at the venue.
Will tickets be available at the door?
Only if we don’t sell out in advance. To secure your spot (and the best rate), we strongly recommend purchasing your ticket ahead of time.
Can I get a refund if I can’t attend?
Tickets are non-refundable, but they are transferable. If you can’t attend, you can gift or resell your ticket to someone else (just email us to update the name on file).
Are you ready to take your side gig to the next level? The Gig to Grow Summit is your opportunity to learn from industry experts and connect with a community of fellow entrepreneurs who understand the challenges of scaling a small business.
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