u/Accurate_Act9717

Setting up an Ontario HoldCo now vs. waiting for a Section 85 Rollover on a highly appreciating digital asset?

Hey everyone,

I dont know much about taxes and tax planning. I tried doing my own research, but I was hoping to get some insight from someone whose is knowledgeable about this stuff. I’m looking for some tax planning info about a cryptocurrency asset I hold long-term in cold storage.

So based on institutional utility and the shift in regulations, I have a strong belief in this specific digital asset and it's the potential for extreme, massive generational appreciation (think Bitcoin level). I am keeping the asset name anonymous to avoid debates; I just want to get insight into the Ontario/CRA tax mechanics for structuring and handeling this growth.

My ultimate goal is to hold this asset inside a corporation to protect it, use it to get institutional yield, and eventually transfer the passive yield through a Family Trust in order to take advantge of benefits which a Trust offers.

My issue is with the timing of when to incorporate and transfer the tokens, and I see two paths:

  • Path A (Incorporate Now): Set up a standard Ontario HoldCorp right now while the asset's price is very low. Transfer the tokens into the corporate wallet immediately. (But anything can happen and I would be wasting money setting up and maitaining the Corp)
  • Path B (Wait and do a Section 85 Rollover): Wait until the asset actually hits a major milestone price (proving the thesis), then hire a tax lawyer to execute a Section 85 Rollover to defer the personal capital gains tax upon transfer. (I heard that doing a Section 85 Rollover after price appreciation limits the advanteges of a Corp?)

My specific questions are:

  • Which path to take?
  • With either path that I choose, can I still successfully set up a Family Trust later on to reduce taxes and get all the structural advantages that come with a trust?
  • Are there any specific CRA anti-avoidance traps I need to be aware of if a regular Ontario corporation is used strictly to buy, hold, and eventually earn institutional yield on digital assets?

Just a reminder: Nothing in crypto is certain. This entire plan is based strictly on my personal opinion and thesis for this specific token. (most people in the crypto space belives that their token is the next Bitcoin, lol). The token that I am betting on could completely flop and I am completely comfortable with that, as I am working within the framework of my financial situation. I just want to get the tax information on these two structural paths.

Appreciate any insight!

Thank you!

reddit.com
u/Accurate_Act9717 — 5 days ago

Setting up an Ontario HoldCo now vs. waiting for a Section 85 Rollover on a highly appreciating digital asset?

Hey everyone,

I’m looking for some tax planning insight regarding a specific cryptocurrency asset I hold long-term in cold storage. I have a clean paper trail of my original purchases.

Based on institutional utility and upcoming regulatory shifts, I have a strong belief this specific digital asset has the potential for extreme, massive generational appreciation (think Bitcoin level). I am keeping the asset name anonymous to avoid speculative debate; I just want to focus purely on the Ontario/CRA tax mechanics for structuring and handeling this growth.

My ultimate goal is to hold this asset inside an Ontario corporation to eventually protect it, use it to get institutional yield, and eventually route the passive yield through a Family Trust to income-split with my family.

I am stuck on the timing of when to incorporate and transfer the tokens, and I see two paths:

  • Path A (Incorporate Now): Set up a standard Ontario HoldCo right now while the asset is sitting at a very low dollar value. Transfer the tokens into the corporate wallet immediately. (But anything can happen and I would be wasting money setting up the Corp)
  • Path B (Wait and do a Section 85 Rollover): Wait until the asset actually hits a major milestone price (proving the thesis), then hire a tax lawyer to execute a Section 85 Rollover to defer the personal capital gains tax upon transfer. (I heard that doing a Section 85 Rollover after price appreciation limits the advanteges of a Corp?)

My specific questions are:

  • Which path to take?
  • With either path that I choose, can I still successfully inject a Family Trust later on to reduce taxes and secure all the structural advantages that come with a trust?
  • Are there any specific CRA anti-avoidance traps I need to be aware of if a regular Ontario business corporation is used strictly to buy, hold, and eventually earn institutional yield on digital assets?

Just a quick cautionary note: Nothing in crypto is certain. This entire plan is based strictly on my personal opinion and thesis for this specific token. There is a real chance that the asset could completely flop and I am completely comfortable with that, as I am working within the framework of my financial situation. I just want to get the tax information on these two structural paths.

Appreciate any insight!

Thank you!

reddit.com
u/Accurate_Act9717 — 5 days ago
▲ 0 r/cantax

Setting up an Ontario HoldCo now vs. waiting for a Section 85 Rollover on a highly appreciating digital asset?

Hey everyone,

I dont know much about taxes and tax planning. I tried doing my own research, but I was hoping to get some insight from people who are knowledgeable about this stuff. I’m looking for some tax planning info about a cryptocurrency asset I hold long-term in cold storage.

So based on institutional utility and the shift in regulations, I have a strong belief in this specific digital asset and it's the potential for extreme, massive generational appreciation (think Bitcoin level). I am keeping the asset name anonymous to avoid debates; I just want to get insight into the Ontario/CRA tax mechanics for structuring and handeling this growth.

My ultimate goal is to hold this asset inside a corporation to protect it, use it to get institutional yield, and eventually transfer the passive yield through a Family Trust in order to take advantge of benefits which a Trust offers.

My issue is with the timing of when to incorporate and transfer the tokens, and I see two paths:

  • Path A (Incorporate Now): Set up a standard Ontario HoldCorp right now while the asset's price is very low. Transfer the tokens into the corporate wallet immediately. (But anything can happen and I would be wasting money setting up and maitaining the Corp)
  • Path B (Wait and do a Section 85 Rollover): Wait until the asset actually hits a major milestone price (proving the thesis), then hire a tax lawyer to execute a Section 85 Rollover to defer the personal capital gains tax upon transfer. (I heard that doing a Section 85 Rollover after price appreciation limits the advanteges of a Corp?)

My specific questions are:

  • Which path to take?
  • With either path that I choose, can I still successfully set up a Family Trust later on to reduce taxes and get all the structural advantages that come with a trust?
  • Are there any specific CRA anti-avoidance traps I need to be aware of if a regular Ontario corporation is used strictly to buy, hold, and eventually earn institutional yield on digital assets?

Just a reminder: Nothing in crypto is certain. This entire plan is based strictly on my personal opinion and thesis for this specific token. (most people in the crypto space belives that their token is the next Bitcoin, lol). The token of that I am betting on could completely flop and I am completely comfortable with that, as I am working within the framework of my financial situation. I just want to get the tax information on these two structural paths.

Appreciate any insight!

Thank you!

reddit.com
u/Accurate_Act9717 — 5 days ago

I am looking for something to boost my GPA, which one do you guys recomend?

NUT 1150 with Caroline Wallace.
NUT 1304 with Charles Dabone (Virtual)
NUT 1104 with Ahmed Gomaa (Virtual)

Thanks

reddit.com
u/Accurate_Act9717 — 18 days ago

Hey everyone,

I’m thinking about switching from an Honours BA in English to a Geography program "Honours BA with a Major in Geography + Minor in English".

I’ve already done about 2 years of English, but honestly I’m burnt out from it and don’t want my last years to be heavy English seminars. Geography seems more interesting, especially the human side, but I have a few concerns and I’d really appreciate hearing from people actually in the program.

My Concerns:

  • How technical is Geography really?
  • Is it science/data heavy?
  • How hard are the physical geography and GIS courses? (I have trouble with chemistry/physics/math)
  • How is the workload compared to English courses?
  • What is your overall experience with Geography?

My situation:

  • Planning to apply to Teacher’s College later (English + Geography teachables)
  • Want to keep a 4-year degree
  • Prefer less technical / less science-heavy courses
  • Trying to protect my GPA

If you’ve been in Geography I’d love to hear:

  • What surprised you about the program
  • What courses/profs to take or avoid
  • Whether you’d recommend it for someone coming from an arts background

I would love any insights! Thanks 🙏

reddit.com
u/Accurate_Act9717 — 19 days ago

I’m an English major looking for an elective, and GEG 2320 (GIS and the Digital Earth) caught my eye. the proff is Roxanne Frappier.

I’ve never taken a Geography class, and more importantly, I’ve never done a lab before and they sound a bit intimidating.

Couple of questions:

  • Do I need math skills for this course?
  • I am not wizard when it comes to computres, should I still take this course?
  • Hows the workload? I am not looking for something crazy over the summer.

Thank you!

reddit.com
u/Accurate_Act9717 — 25 days ago