Thanks for sharing - everything seems sound based on an 'all-weather' style strategy, with your Silicon Valley insider-bent.
To make it more detailed, any chance you could share rough returns in each of these categories over time, and have you made any changes to the allocations based on that?
Also, in terms of stock picking - do you buy directly or do you ever leverage it and buy options? Any major misses or do you always pick winners ;-)?
On the VC side, I've invested in, if I had to guess, 15-20 venture funds. I can't think of one that hasn't returned at least 1x, that said, the worst performers in this class have returned that 1x over a number of years, which has underperformed other (more liquid) markets. I have one specific AI fund that looks to be (on paper) a promising 10x+, but again, early days. Blended, I'd say 3-5x over 5-10 years is a fantastic fund.
Without a doubt my angel investments have been the most lucrative, but that's (as the article pointed out) a combination of right place/right time and access.
Major misses, plenty. I'd say the vast majority was due to not holding long enough. There have been quite a few times when a 5x was a huge win, but there was another 100x+ waiting had I just been patient. This can obviously also cut the other way (NFTs).
Venture investments seem only like a good idea if you have access. By the time even most 'accredited' investors see a deal it's too late - just ask your university endowment CIO...
Thanks for the detail Kevin! Surprised by the relatively low crypto allocation given your involvement in the space. Is a couple % bitcoin the entirety? And where do you bucket NFTs?
Part of my venture fund investments hold crypto company equities, tokens, and NFTs (I'm still a member of Flamingo DAO, a great NFT index DAO), so I don't need to take on additional exposure. But yes, on the self directed personal side, just BTC in retirement accounts.
Thank you Kevin! Always appreciated your take. I miss the modern finance pod. How do you think about real estate? Not personal residence, but cash flowing properties?
A few of my friends love this and do it quite successfully. I especially like the strategy when interest rates were low you could buy property and then take cash back out and keep the delta against market returns. That said, the friends that I have that do this realize it’s almost a full-time job or they need to hire a property manager For me, I’d rather keep it simple or add in a reit fund (but I don’t). *siri
Thank you being so transparent and sharing.. you’ve spoken previously about financial advisors, curious to know what value they are bringing as you seem to have such a good handle on your money.
They are great at managing capital calls, reviewing investment documents, buying laddered bonds (can be a pain in the ass, but now I use Wealthfront for that), helping with tax document handoffs, setting up trusts, helping with home loans, and being a great thought partner etc. etc.
That said, for most, I think a service Facet (flat fee) can help with most of this: https://facet.com/ vs some face big name private wealth mgmt service.
I still hold NVIDIA today, largely because I still see a moat there for the foreseeable future. That said, it's hard to invision another large multiple increase anytime soon. If I didn't already have a position I'd likely be content that 6.22% of the VOO index (S&P 500) is NVIDIA.
Regarding Tesla, they are dealing with a packed EV market, and Elon's stirring up more drama these days. I need more than just another car from them. I'm hoping for more technical innovation and sitting on the sidelines until then.
What are your thoughts around re-balancing, especially in the fortunate circumstance when the high-risk portion has exponential gains. I struggle knowing when to sell, how much, tax consequences, etc. Do you have any set rules on re-balancing?
Have you looked at Fundify? They have an interesting model for getting everyday investors access to interesting early stage deals. My friend Josh Chodniewicz (founder of Art.com whose vc fund was the lead investor in my last company) is the founder.
Thank you Kevin, this i svery insightful and puts on paper many of the things I am currently doing. How do you deal with the volatility of bitcoin? it started as a 2% of my portfolio but it has reached almost 10% in some peaks. Do you sell to adjust to 5% or keep it even if it becomes 20% of your portfolio?
Interesting discussion about gold. I've heard the comments many times about how gold isn't a good investment, and I think there's some confusion about gold as a commodity investment, physical gold, etc. I made the decision last year to put about 20% of my portfolio in GLD, which is a gold-backed ETF, and it has outperformed 2 of my Vanguard high-yield dividend funds over the past 12 months. This creeps into the ETF discussion as well, but I think the overall message that gold is a bad portfolio move is just misguided.
Thanks for being open about your investments. You mentioned you declared bankruptcy back in 2000ish. Without wanting to open old wounds how did that affect your future approach to investing?
Thank you for sharing this. Could you please expand on when and how you sell positions? Do you begin to taper out when valuations are heated - somewhat dollar averaging out of a position - or get out completely once the thesis is breaking or broken?
Would also love to see more detailed examples of past investment theses and how you entered and exited them!
I hear ya, but if your horizon is multi-decade, I'd rather just buy and hold, sleep at night, etc., and have my energy go towards looking for the next big thing vs optimizing for volatility. That said, my buddy Mike does this all day long and loves the game of it all :)
Thanks for sharing - everything seems sound based on an 'all-weather' style strategy, with your Silicon Valley insider-bent.
To make it more detailed, any chance you could share rough returns in each of these categories over time, and have you made any changes to the allocations based on that?
Also, in terms of stock picking - do you buy directly or do you ever leverage it and buy options? Any major misses or do you always pick winners ;-)?
Sure.
On the VC side, I've invested in, if I had to guess, 15-20 venture funds. I can't think of one that hasn't returned at least 1x, that said, the worst performers in this class have returned that 1x over a number of years, which has underperformed other (more liquid) markets. I have one specific AI fund that looks to be (on paper) a promising 10x+, but again, early days. Blended, I'd say 3-5x over 5-10 years is a fantastic fund.
Without a doubt my angel investments have been the most lucrative, but that's (as the article pointed out) a combination of right place/right time and access.
Major misses, plenty. I'd say the vast majority was due to not holding long enough. There have been quite a few times when a 5x was a huge win, but there was another 100x+ waiting had I just been patient. This can obviously also cut the other way (NFTs).
Thanks for sharing.
Venture investments seem only like a good idea if you have access. By the time even most 'accredited' investors see a deal it's too late - just ask your university endowment CIO...
Thanks for the detail Kevin! Surprised by the relatively low crypto allocation given your involvement in the space. Is a couple % bitcoin the entirety? And where do you bucket NFTs?
Part of my venture fund investments hold crypto company equities, tokens, and NFTs (I'm still a member of Flamingo DAO, a great NFT index DAO), so I don't need to take on additional exposure. But yes, on the self directed personal side, just BTC in retirement accounts.
Thank you Kevin! Always appreciated your take. I miss the modern finance pod. How do you think about real estate? Not personal residence, but cash flowing properties?
A few of my friends love this and do it quite successfully. I especially like the strategy when interest rates were low you could buy property and then take cash back out and keep the delta against market returns. That said, the friends that I have that do this realize it’s almost a full-time job or they need to hire a property manager For me, I’d rather keep it simple or add in a reit fund (but I don’t). *siri
Thank you being so transparent and sharing.. you’ve spoken previously about financial advisors, curious to know what value they are bringing as you seem to have such a good handle on your money.
They are great at managing capital calls, reviewing investment documents, buying laddered bonds (can be a pain in the ass, but now I use Wealthfront for that), helping with tax document handoffs, setting up trusts, helping with home loans, and being a great thought partner etc. etc.
That said, for most, I think a service Facet (flat fee) can help with most of this: https://facet.com/ vs some face big name private wealth mgmt service.
This is actually great shit!
Would you still buy Tesla or NVIDIA today?
Not finance advice, but my take:
I still hold NVIDIA today, largely because I still see a moat there for the foreseeable future. That said, it's hard to invision another large multiple increase anytime soon. If I didn't already have a position I'd likely be content that 6.22% of the VOO index (S&P 500) is NVIDIA.
Regarding Tesla, they are dealing with a packed EV market, and Elon's stirring up more drama these days. I need more than just another car from them. I'm hoping for more technical innovation and sitting on the sidelines until then.
What are your thoughts around re-balancing, especially in the fortunate circumstance when the high-risk portion has exponential gains. I struggle knowing when to sell, how much, tax consequences, etc. Do you have any set rules on re-balancing?
I was wondering this too. Any rules for getting bonds back up from 0%?
Have you looked at Fundify? They have an interesting model for getting everyday investors access to interesting early stage deals. My friend Josh Chodniewicz (founder of Art.com whose vc fund was the lead investor in my last company) is the founder.
Hey Kevin, thanks for the insightful write-up. For your kids, what are your thoughts on 529 plans?
Thank you Kevin, this i svery insightful and puts on paper many of the things I am currently doing. How do you deal with the volatility of bitcoin? it started as a 2% of my portfolio but it has reached almost 10% in some peaks. Do you sell to adjust to 5% or keep it even if it becomes 20% of your portfolio?
Interesting discussion about gold. I've heard the comments many times about how gold isn't a good investment, and I think there's some confusion about gold as a commodity investment, physical gold, etc. I made the decision last year to put about 20% of my portfolio in GLD, which is a gold-backed ETF, and it has outperformed 2 of my Vanguard high-yield dividend funds over the past 12 months. This creeps into the ETF discussion as well, but I think the overall message that gold is a bad portfolio move is just misguided.
Thanks for being open about your investments. You mentioned you declared bankruptcy back in 2000ish. Without wanting to open old wounds how did that affect your future approach to investing?
Thank you for sharing this. Could you please expand on when and how you sell positions? Do you begin to taper out when valuations are heated - somewhat dollar averaging out of a position - or get out completely once the thesis is breaking or broken?
Would also love to see more detailed examples of past investment theses and how you entered and exited them!
Thoughts on covered calls ETFs (potentially less volatility, dividend)?
I hear ya, but if your horizon is multi-decade, I'd rather just buy and hold, sleep at night, etc., and have my energy go towards looking for the next big thing vs optimizing for volatility. That said, my buddy Mike does this all day long and loves the game of it all :)
Amazing, thanks for adding that here I wasn’t aware of that, I’ll have to look into it more.