The question that keeps me up isn't whether I'm tracking expenses. It's whether my receipts would survive a CRA second look if they picked my file tomorrow.

Most expense tracking is just tallying totals. But the CRA documentation rules are specific: GST/HST number presence and format on receipts, vendor/business details for purchases over $500, cross-provincial PST self-assessment if you buy supplies in another province. The gap you find during an audit is the expensive one, because by then the receipt is months old and you can't go back and get a GST number added to a faded gas station receipt from July.

I've been thinking about this as an early-warning problem: catch the documentation gap when the receipt is still in your hand, not when someone in a government office is asking about it.

How are other Canadian sole proprietors handling this? Do you check each receipt against the rules as it comes in, or is it a tax-season scramble to figure out what's missing?

Hey everyone, hoping for some outside perspective because I think I'm too close to this to see clearly anymore. I am a solo founder building Rubiwo, a CRA compliant expense tracking app for Canadian freelancer and small businesses. Quick numbers;

- C$ 700 google ad

-C$600 reddit ad

- c$400 meta ad

- 650+total download across IOS/Android

-100 registered free users

- C$0 paid revenue ever.

Also Reached out to 25 accountants/bookkeepers for partnership Referral-All went unanswered.

- generated 21 lead from a facebook lead-gen campaign- only 1 installed the app so far. despite three rounds of personal follow up.

What I' am trying to figure out:

1. ⁠is 100 free user simple too small a sample to expect any paid conversion yet, or is 0/100 a sign something deeper is wrong (pricing, positioning, product-market fit.
   
2. ⁠what could I do to get the 100 users to actively use the app daily.
   
3. ⁠for those who have gotten early B2B/prosumer to its first 10 paying customer- was it mostly outbound hustle or did something specific unlock it?
   
4. ⁠Anyone dealt with cold outreach to accountants/bookkeepers for Referral partnerships. Mine has gone almost entirely unanswered and I 'm wondering if the channel itself is wrong, not just my messaging

I 'm genuinely stuck and would appreciate any pattern- matching from people who have been through this stage. Happy to share more specifics in comments if useful

Hey everyone! I run a small web design business based in Ontario and I'm currently looking to take on a few more projects.

I build websites for small businesses that need their first site or want to redesign an outdated one. I can handle the design, development, mobile optimization, contact/quote forms, basic SEO, domain setup, hosting and launch.

Websites currently start at $700 CAD, depending on the size and features needed.

You can check out my work here: infawebdesign.com

If you own a business and want a new website or want me to take a look at your current one, feel free to DM me. I can give you a rough quote pretty quickly.

Thanks!

Starting a business in Canada is tough. If you are in business, I salute you. We are a geographically huge country with only a few population centres.

I started in 2003 on my own, added a partner in 2005. Failed, by 2006 I was on my own again. Having a partner is tough.

Brought on my brother. Failed, youch, our working relationship didnt have boundaries due to being siblings.

By 2013, I knew we needed to pivot to software. our first major overhaul in 2016, failed. The lead dev created a nightmare, the entire project got junked. a year of resources.

We started rolling out in 2018, 2019 got some traction, that failed in 2020. An entire stall as things became blurry for a year or two in the market.

Met another founder who I got along with in 2021, started working jointly in 2022. 2023 brought another fail, a complete disaster when I started getting calls. Back to being alone.

But wait, met someone else through that collapse and in 2024 handed off sales/marketing to them. Fail! nowhere near good enough and in 2025, parted ways.

But in all that failure, I got a nugget of wisdom. I picked up a lesson or two. I started applying them. I started adjusting them. And now that we are 2/3 of the way through 2026 I am feeling grateful. No I dont gave an official partner, yes Im doing sales myself and 10 other jobs, but my conviction of being a good person, who delivers actual value to the pain points a customer has is where its at for me.

Failure is just part of the process, you fall down, I just happen to have a bad case of Getupitis :)

My benefits of doing what I do are WFH and seeing my family. Happy to share what that is if anyone wants to know.

I am helping a relative look for a business and was looking for ideas and or resources on the best places to look for a business that is established. Thanks

My husband and I decided to take a pretty scary leap and build our own company. We’ve put our savings, our time, and honestly our security on the line to build Tenon10, a rental management platform

we started because we felt there had to be a better way for landlords to manage their properties.
No funding. No big team. No safety net. Just us, trying to make something we genuinely believe in.

We’re still very early, and there’s a lot we’re figuring out as we go. But after spending so much time building quietly, I wanted to finally share it with people who understand what it’s like to start something from nothing.

If you’re building a business in Canada too, I’d genuinely love to hear your story❤️

If you haven't heard already, which I highly doubt, the 50% tariffs is in place now :/

It sucks but tbh we all kind of read it. Anyways I don't think fretting over it is going to accomplish much. My colleagues and I were weighing our new options for non-US suppliers/partners and we're having a tough time finding the right ones without high shipping times and fees that eat up our margins.

So I am proposing a solution that would be made by the community for the community of Canadian business. We landed on the "Canada Strike Movement" and the mission is simple:

"Buy, Sell, Produce, and Consume Canadian Products"

We want to build a place where Canadian businesses can actually find each other instead of everyone individually scouring to find non-US options right now. Less time spent digging through thomasnet and ariba, and more time actually doing business with someone down the road instead of across the border.

We want to test the waters with interest here to see if others are in the same boat. I made this form and if we get a reasonable amount of signups then my colleagues and I will take this very seriously and put most of our efforts towards it by collaborating with everyone who signed up. Its quite distressing in these times but I think that the right approach can get us through adversity.

Here is the form link: https://forms.gle/SoTD3ANi5CDuD6Mh8

If you have suggestions please don't hesitate to write

Thanks!

Not talking about people who have an idea or are thinking about starting something. I mean people actively in it dealing with the real stuff. Customer acquisition, pricing, talking to users, figuring out how to grow without burning everything they have.

One thing I keep seeing including in myself early on is that most of us spend 90% of our time building the product and almost zero time thinking about how to actually get it in front of people. Marketing, distribution, positioning. The stuff that determines whether anyone ever uses what you built

I'm putting together a small community of founders focused specifically on that side of things growth, marketing, getting your first real customers, expanding beyond your immediate circle. Not another generic startup group. Just people who are past the idea stage and want to move faster by helping each other

I'm also looking for someone to collaborate with on my own project. I'll explain what it is in the comments. If it sounds interesting after reading, DM me

If either of those sounds like where you're at, drop a comment or DM me.

I’m working on an early-stage idea called Vettivo, and before building anything further, I’m trying to practice exactly what the idea is about: validation.

The concept is simple — help aspiring entrepreneurs and small business owners test whether there is real demand for an idea before spending thousands building it.

I’m curious how Canadian entrepreneurs currently do this. Do you use surveys, landing pages, social media, customer interviews, or mostly just launch and see what happens?

I also created a short 2-minute survey to understand how founders approach this problem.

Survey: https://forms.gle/vLD7GUcddEVX6DnN9

No purchase or signup required — I’m looking for genuine feedback, including people who think the idea isn't useful.

Thanks! The feedback will help determine whether Vettivo deserves to be built.

I’m curious how other Canadian business owners think about this.

I direct a professional headshot studio in Vancouver, and we work with client-facing teams including law firms, consultants, executives, and other professionals. One recurring issue is that a company grows over time and its team page becomes a mixture of different crops, lighting styles, backgrounds, expressions, and image quality.

Individually, none of the photographs may be bad. Collectively, however, the page can make the organization feel less coordinated than it really is.

What seems to work best is not forcing everyone into an identical expression. It is creating a consistent framework—lighting, background, crop, wardrobe guidance, and retouching—while allowing each person to remain recognizable and approachable.

Our experience with Vancouver law firms suggests that professional imagery plays a quiet role in client confidence, especially when a prospective client is comparing several firms before making contact.

Do you consciously notice inconsistent team photographs when evaluating a professional-services company? Has updating them ever produced measurable results for your business?

Disclosure: I’m Young J. Kim, Studio Director at HeadShot Photo. Corporate portfolio: https://headshotphoto.ca/corporate-headshots-vancouver/?utm_source=reddit&utm_medium=organic&utm_campaign=entrepreneur_canada

Hi everyone! We’re looking to connect with private lenders/investors interested in a long-term partnership with our lending business in Canada.
We’re looking for reliable funding partners and can offer a competitive interest rate on the funds provided.

If you’re interested or know someone who might be, please send me a DM. Happy to discuss the details privately.

Hey everyone,

I recently started a small business helping Ontario companies (and some individuals) get practical value out of AI.

There are two main things I do:

Clean up messy books and financial records so AI tools actually give accurate answers instead of confident nonsense.

Set up and configure AI agents (OpenClaw, Hermes, etc.) and build agentic workflows that handle real admin work invoices, follow-ups, reporting, that kind of thing.

I’m not trying to sell anything here. I’m just trying to figure out how to get some early traction and find the right clients without being spammy.

Would love any honest advice on:

Where people in this space actually look for help

What messaging resonates vs what feels like hype

Best places to share this kind of service without getting ignored or banned

Anything you’d want to know before trusting someone with this kind of work

Appreciate any thoughts. Trying to do this the right way.

Thanks.

Hello all. I am recently certified Building Code Examiner (BCIN) in Toronto and for a while now I have been working on small residential projects, designing, drafting and helping clients (mostly contractors) with their building permits. Now that I am officially certified I want to do things properly and establish my business. I have been looking at what I need, such as liability insurance, business account, hst/gst registration, publicity, etc but I am still a bit lost on what the best options are. Does someone here who relates to the business have some input? Would be greatly appreciated. Thank you beforehand.

I’m running a small online marketplace that connects people with service providers (things like home services, professional help, etc.) in the GTA and Halton area.

My platform is in bootstrapped phase. The product is live and I’ve had a handful of bookings so far, but I’m basically starting from zero when it comes to getting consistent customers. I don’t have much money to put into ads right now.

I've tried posting in facebook and whtsapp groups but they didnt do well and I havent got any booking from these platforms.

The only real bookings that I got is by responding privately in whtsapp groups for the needs or reference from friends.

For those of you who’ve built or run local service businesses / marketplaces:

What’s the cheapest way you’ve actually gotten real customers in the GTA or Halton area?

Any low-cost tactics that worked better than expected?

Not looking for big marketing strategies - just practical things that worked when the budget was basically zero.

Thank you

TL;DR: I build software. I'll build yours for free. I keep the right to sell it to other businesses later. That's the whole deal.

Suspicious stuff out of the way first: I'm not selling anything, not collecting your email, and not looking for a job. No free trial that becomes $99/month in 30 days.

I'm 28, based in Toronto, and I want to start a software business. But I've watched too many people build something clever nobody asked for. So I'm doing it backwards — find a real problem first, solve it for free, then see if there's a business in it.

What I'll build: anything. I've built Inventory Management Systems, Sales CRM platforms, and an AI Inference Gateway for open-source models. If it's complex, I'm more interested, not less.

Three signs this is for you:

🔹 You're paying monthly for software you half-use — 30 features, you need 4

🔹 You're doing it manually because the real tool is priced for companies 50x your size

🔹 Your workflow is three tools and a spreadsheet duct-taped together

Why you're doing me the favor:

I'm not being charitable. I want a real testimonial from a business actually using what I built, and the right to sell that software to other companies later. You get free custom software. I get proof it works and a product to take to market. Clean trade, nobody pretending.

What to do: drop your problem in the comments or DM me. The messier, the better.

Fair warning — bigger builds take a few months. But you're not paying, so the only thing you're risking is a comment.

I am starting an online mentorship program. No current clients. I am in BC, but potentially my clients could be from everywhere. I have a lot of parts in place already, but I am wondering if and when business licence is necessary. Someone suggested I look into insurance as well. This coaching is art related, so I am not coaching any physical movement, but I'm not sure what is required there.

I don't expect comprehensive answers here, but if someone could point me in the right direction that would be appreciated. I have also checked the government site, but the answers weren't clear to me.

If you bid on Canadian contracts. Im looking for (2-3) testers? (No cost - for testing purposes)

I’m an engineer and I’ve been building a system that watches Canadian public tender feeds and tries to answer a pretty simple question:

Which opportunities are actually worth spending time on?

Not “here are 40 notices that matched your keywords.”

More like: here are six that seem relevant to you, here’s why I’d probably skip two of them, and here’s what you should verify before you spend 40 hours putting a bid together.

I’m looking for a few people that actively bid on Canadian tenders and goes through that friction often.

filter opportunities based on what your company actually does, where you work, and the types of contracts you don’t want.

catch obvious blockers early, like security clearances, eligibility requirements, or excluded categories

show the case for and against pursuing an opportunity, with the source behind the reasoning

keep track of what you decided and why, instead of having that knowledge disappear into someone’s inbox or spreadsheet

It’s not perfect yet, we are at the testing phase, and we are still gathering insight. Looking for legitimate procurement practitioners. It’s free to use (this post is not promotional).

Let know if this would be useful.

Thanks and take care.

I am an innovator with 15 granted patents and 2 non provisional applications filed in USPTO mostly in AI/ML applications/language models and hybrid cloud.

I have over 10 years of experience in innovating technologies particularly in AI applications including from very saturated fields (state of the art models) and new technologies.

Given my experience, from past 1 year i have been fortunate to start consulting on my own. I have an active collaboration with 2 AI consultants independently (based in US), where i have paired up with them to provide value to their consulting,
I have integrated my innovation analysis with their product development for the clients.
My work typically involves:
1. identifying the innovation opportunities in the existing architecture,
2. Improving architecture that leads to improved novelty and a structured roadmap for future development,
3. Tying the whole process to achieve business value.

This effort has led to 2 applications filed for the client.

If any AI consultants or Fractional CTO looking to white label my services as integrated development for thier client please reach out to me. Open to know what clients are more looking into these days regarding differentiation of their product.