I decided to keep a running list of some of the mistakes I’ve made in crypto in roughly chronological order. Enjoy!





Ignoring Bitcoin in 2010.
I built a hackintosh desktop for fun and was looking for ways to make money off it. I found out about mining Bitcoin, but it would raise my parent’s electricity bill by $10-30/mo. Given the lack of liquidity — only OTC trades on forums — why bother!?
I built a hackintosh desktop for fun and was looking for ways to make money off it. I found out about mining Bitcoin, but it would raise my parent’s electricity bill by $10-30/mo. Given the lack of liquidity — only OTC trades on forums — why bother!?
Ignored Bitcoin in 2010 V2
I saw the Bitcoin talk post in 2010 offering 10,000 BTC for $50.
I offered something like $35 and thought he’d haggle. He wouldn’t. I was more offended by his refusal to haggle than caring about the price and didn’t bother.
I saw the Bitcoin talk post in 2010 offering 10,000 BTC for $50.
I offered something like $35 and thought he’d haggle. He wouldn’t. I was more offended by his refusal to haggle than caring about the price and didn’t bother.
Ignored Bitcoin 2011
I made

buying gold options when it looked like US may default on our debt. I started looking into non-custodial alternative assets (art, comics, etc) and rediscovered Bitcoin. Didn’t want to give passport to MtGox, so I ignored it.
I made



Butterfly Labs 2013
Pre-ordered several Butterfly Labs miners. Didn’t arrive in 6 months after I placed the order. Luckily @AmericanExpress refunded me on last day of eligibility.
Lost on huge BTC gains during that period.
“Just 2 more weeks!”
Pre-ordered several Butterfly Labs miners. Didn’t arrive in 6 months after I placed the order. Luckily @AmericanExpress refunded me on last day of eligibility.
Lost on huge BTC gains during that period.
“Just 2 more weeks!”
Peercoin Change Address 2013
Losing $70,000 of Peercoin (value at the time) during the 2013 bubble. I didn’t realize they weren’t using HD wallets in Peercoin main client. Would’ve timed that bubble pop perfectly.
Losing $70,000 of Peercoin (value at the time) during the 2013 bubble. I didn’t realize they weren’t using HD wallets in Peercoin main client. Would’ve timed that bubble pop perfectly.
Not working for Coinbase 2014 1/2
I didn’t even apply, but (perhaps arrogantly) assume I could’ve gotten a position as the crypto world was tiny and I was one of the few who really got the space
My reasoning? Thought their most recent VC round didn’t leave me much upside
I didn’t even apply, but (perhaps arrogantly) assume I could’ve gotten a position as the crypto world was tiny and I was one of the few who really got the space
My reasoning? Thought their most recent VC round didn’t leave me much upside
Not working for Coinbase 2014 2/2
I assumed that Coinbase’s max market cap was $3B, and that’d be a stretch. Didn’t seem like a good risk-reward.
After all...EVERY bank and financial institution was just around the corner from selling BTC in your bank and brokerage account.
I assumed that Coinbase’s max market cap was $3B, and that’d be a stretch. Didn’t seem like a good risk-reward.
After all...EVERY bank and financial institution was just around the corner from selling BTC in your bank and brokerage account.

Underestimating @VitalikButerin 2014
I subscribed to @BitcoinMagazine and was floored by how clearly this guy Vitalik repeatedly wrote on complex topics.
Saw the Ethereum WP & loved it. But only put 1% of BTC holdings into Ethereum ICO. Still ended up being life changing!
I subscribed to @BitcoinMagazine and was floored by how clearly this guy Vitalik repeatedly wrote on complex topics.
Saw the Ethereum WP & loved it. But only put 1% of BTC holdings into Ethereum ICO. Still ended up being life changing!
Selling ETH after the DAO hack 2016
Sold my entire stack of ICO ETH after the DAO hack at ~$7-10/ETH. If these guys couldn’t write an unhackable contract, then dApps probably couldn’t be coded securely.
I FOMOd back in at $25/ETH, reducing my total ETH by >2/3 from ICO.
Sold my entire stack of ICO ETH after the DAO hack at ~$7-10/ETH. If these guys couldn’t write an unhackable contract, then dApps probably couldn’t be coded securely.
I FOMOd back in at $25/ETH, reducing my total ETH by >2/3 from ICO.
Not raising an ICO for my prior company 2017 1/2
We had $50M lined up to buy my company’s ICO. Our lawyers insisted we’d be breaking money transmitter or securities laws. I, as CEO, could go to jail. I killed the offering. The govt has since not prosecuted for what we panned.
We had $50M lined up to buy my company’s ICO. Our lawyers insisted we’d be breaking money transmitter or securities laws. I, as CEO, could go to jail. I killed the offering. The govt has since not prosecuted for what we panned.
Not raising an ICO 2/2
I’m not for these rules, but by not enforcing what’s on the books, only the most sketchy people win.
We moved forward w/ a Reg-D offering. I’ll leave it at we worked w some liars & everything took so long the deal fell apart as the market crashed in 2018
I’m not for these rules, but by not enforcing what’s on the books, only the most sketchy people win.
We moved forward w/ a Reg-D offering. I’ll leave it at we worked w some liars & everything took so long the deal fell apart as the market crashed in 2018
Not selling during the 2017 Bubble 1/2
When Coinbase hit most downloaded iOS app in December 2017, I knew it was time to sell. I’m very good at timing bubbles (but this is about failures!).
I didn’t sell my entire crypto stack bc I didn’t want to worry about taxes.
When Coinbase hit most downloaded iOS app in December 2017, I knew it was time to sell. I’m very good at timing bubbles (but this is about failures!).
I didn’t sell my entire crypto stack bc I didn’t want to worry about taxes.
Not selling during the 2017 Bubble 2/2
IRS was changing guidelines around crypto taxes and, scarred from the summer 2017 ICO attempt, didn’t want to sell everything (sold some) w/o rules clarified.
I figured we’d go down maximum 60% ($8k BTC) and then bounce back to $12k. Nope!
IRS was changing guidelines around crypto taxes and, scarred from the summer 2017 ICO attempt, didn’t want to sell everything (sold some) w/o rules clarified.
I figured we’d go down maximum 60% ($8k BTC) and then bounce back to $12k. Nope!
Not buying $SNX earlier 2018/19
I read the Havven WP and thought it was an idiotic scam. Heard about Synthetix in Jan 2019 from @DegenSpartan. Immediately wrote it off bc it evolved from Havven.
Degen introduced me at <$0.02(?). Kept making good points. I buy in at $0.08-0.11
I read the Havven WP and thought it was an idiotic scam. Heard about Synthetix in Jan 2019 from @DegenSpartan. Immediately wrote it off bc it evolved from Havven.
Degen introduced me at <$0.02(?). Kept making good points. I buy in at $0.08-0.11
Not buying a @helium hotspot in summer 2019
Because it was so close to my company’s ICO proposal, I knew it was a good idea. But I didn’t want to spend $500/AP and drive up my electricity bill. What is it w me and electricity!
Because it was so close to my company’s ICO proposal, I knew it was a good idea. But I didn’t want to spend $500/AP and drive up my electricity bill. What is it w me and electricity!

Not buying BZX insurance on Nexus Feb 2020
I interacted w one of the BZX members and saw the way he ignored security. I tried to take out $80,000+ cover on Nexus for ~$90, but Nexus demanded I verify w a passport. Nope, wouldn’t do it! Something like 10 days later, BZX hacked.
I interacted w one of the BZX members and saw the way he ignored security. I tried to take out $80,000+ cover on Nexus for ~$90, but Nexus demanded I verify w a passport. Nope, wouldn’t do it! Something like 10 days later, BZX hacked.
These are only a fraction of the mistakes I’ve made in crypto. I’m sure I’ll make many more, which I’ll document here once the pain goes away.
But at the end of the day, what matters is we learn from our mistakes and continue to play the game!
But at the end of the day, what matters is we learn from our mistakes and continue to play the game!