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Things I wish someone had told me before I started angel investing

blog.rongarret.info

201–210 of 231 posts

Re: Things I wish someone had told me before I started angel investing

#201
post #38

> But the cool kids don't beg. The cool kids — the ones who really know what they're doing and have the best chances of succeeding — decide who they allow to invest in their companies. The company I was an early employee of (that ended up being a "unicorn") was not a cool kid, and we certainly were begging people to invest both at the angel stage and (especially) the series A stage. And those people got a really real…

How is it that a $10k check even gets a startup to take your call? That pays like one engineer for a month, if that. (Genuinely curious)

It's either part of the entire round, or it's gonna go to a founder, one of whom is an engineer if it's a tech biz, and it'll feed them for 2-3 months while they get the prototype together.

Re: Things I wish someone had told me before I started angel investing

#202

Earlier quoted context omitted.

Fill us in; why did they fail? I've seen a lot in business, and I never saw anything as challenging and perverse as your "creative ways the universe will come up with to screw you". The worst I heard of was law suits by patent trolls. For "secret sauce" in IT, that's in software locked up in the internals in a secure server farm. Tough to know just what is in that. Tough to get a judge to force you to present all you…

1) key employee has an old discounted investment make them independent and they take flight (didn't see that coming.. they seemed all in) 2) dot-com bubble and crash. Simultaneously freezes investment and convinces everyone that internet related startups are hokum. We survived and exited at less than a quarter what we would have had. It didn't matter that we had positive cash flow and gazillions of thrilled customers…

1) Yup, employees can leave. We know that. If have a "key" employee, then need some strong reasons they will stay, and even with those reasons they may leave because of something about their marriage, children, health, etc. If you promised them stock and are 18 months late, then they may get pissed, not trust you, and leave. They may get run over by a truck, etc.

We know that.

That's why the founder should be the main key employee. Or, if have a key employee, then maybe they should have a deputy that can fill in in case of an emergency. That's why there are carefully thought out compensation plans for key employees, e.g., unvested stock options.

Once I was in a little company. Since there was some question about my status, I circulated some resume copies. In that little company, some instances of good work I'd recently done made me essential to our business with one potentially good customer and with our main customer. One of the resume copies got me a better job offer, and I took it. As I submitted my resignation letter, soon late at night I got a phone call from the CEO of the little company: He told me that he would accept my resignation "with prejudice" which didn't really mean anything. He was also drunk at the time.

Part of the job of a CEO is to keep key employees happy. That CEO had been treating me as excess baggage, with the mushroom treatment (keep the employee in the dark and feed them BS) until I became important. Then at one point, in the hall, as apparently an off hand comment, with some resentment and no details, elaboration, or discussion, he said "You are becoming an important person around here". Actually I'd just done some work for a week I'd never told the CEO about, work that thrilled our main customer and in effect got us sole source on a competitive software contract. I didn't yet know how important my work was, and I didn't know that my CEO knew anything about it. But apparently some high up guy at our main customer (the US Navy) called my CEO and had a chat about my work. So, as of the mushroom treatment, not letting an employee know they were doing well, etc., my CEO didn't discuss my exceptional work with me. So, all he did was just make the resentful remark in the hall. He was happy as a clam until he got my resignation letter which suddenly put his future with the two customers at risk. He was CEO of the little company, but that little company was just a subsidiary of a much bigger company; so, no doubt, from losing two big chunks of business, the CEO's job was also at risk. He was a dumb CEO.

2) Yup, the year 2000 bubble and crash hurt a lot of startups. But for a startup, the flow of more equity capital is always a really bad crap shoot that can be affected by anything including the hemlines of skirts of teen girls, sun spots, and a war in central Africa, or a drought in the Amazon valley. A startup just CANNOT depend or count on (count chickens before they hatch) on future equity capital. Similarly for future M&A deals.

Instead, if the customers are still happy and the revenue is still there, then that's about the best can hope for; in bad times, commonly anything more than that can be just a red cherry on top of whipped cream on top of ice cream on top of a waffle. Until the bad times pass, what's real is just the waffle. For the going business, just keep that going, be glad there's no second Great Depression, be glad some one customer, the source of 75% of the revenue, doesn't go bust, etc., keep the revenue going, please the existing customers, try to improve the business in promising, incremental ways, accumulate the after tax earnings, keep watching for better times, and be thankful for what do have.

3) Sure, there are lots of ways some lawyers can look for billings. One way is nuisance law suits. So, sure, maybe start your business as a sole proprietorship. As soon as have any decent revenue look into business insurance to protect you from nuisance law suits and pay a lawyer to set you up as an LLC. Then get to relax for a while. If are small, then filing a nuisance law suit against you is not worth the time, expense, and effort. But if are small and some lawyers do file, then -- IANAL but just thinking out loud about what I'd consider doing -- let them sue the LLC. Shutdown the LLC and restart the business under another name; contact the old customers, etc. and keep going under the new name. Also patch the legal hole the lawyers used to attack you. Also, as soon as have any decent revenue, talk to some lawyers and get some protection against nuisance law suits. E.g., I just saw a disclaimer by a major company saying that they don't accept, look at, or use unsolicited ideas from outside -- right away I kept and indexed a copy of that disclaimer and will be sure to use it when and if appropriate. Generally, need some protection against law suits from unsolicited outside contributions -- IANAL, but likely YouTube has some legal walls against such attacks.

Once are a significant company, do check with more than one high end business law firm and business insurance firm on being protected.

4) Sure, can have spies, worms, saboteurs, agents of competitors or unions, thieves, etc. So, use some standard precautions, e.g., the standard rule in security, "need to know". Maybe have some bonded employees. Look into some security firm checking the security of your organization, say, something like a white hat hacker would check the security of your server farm or other computers. Keep the intellectual property crown jewels nicely locked up. When still small, for the daily incremental backup data, maybe have the CEO take those home and store them in a box in his den; have multiple copies of full backups stored with great safety, off site, etc. Make good use of encryption. Etc. Nothing here is new; we're not the first to consider such things; so, there should be some good advice readily available.

Re: Things I wish someone had told me before I started angel investing

#203
post #170

Earlier quoted context omitted.

Fill us in; why did they fail? I've seen a lot in business, and I never saw anything as challenging and perverse as your "creative ways the universe will come up with to screw you". The worst I heard of was law suits by patent trolls. For "secret sauce" in IT, that's in software locked up in the internals in a secure server farm. Tough to know just what is in that. Tough to get a judge to force you to present all you…

> Fill us in; why did they fail? That would take a book. Or at least a lot more blog posts.

If there could be a book, then there's enough for a blog post for the four cases you mentioned.

As it is, you are telling me that during the night aliens will attack my business, leave without a trace, but have my business in ruins by 8 AM in the morning. Your claim is the first I ever heard of such a thing.

Having orders of magnitude better price/performance is amazing. An "order of magnitude" is usually a factor of 10; those are not easy to come by. Leading examples include Moore's law, hard disk drive capacities, solid state disk drive capacities, optical fiber data rates, wireless data rates, and floating point operation rates in GPUs. In any market of any major size, typically customers just LOVE some factors of 10 better price/performance, and any company that is the sole source of such an advantage should have nearly a license to print money. What went wrong? Anxious readers are eager to know! You have an attentive audience waiting!

Re: Things I wish someone had told me before I started angel investing

#204
post #3

My 2 cents - As an investor or potential employee when analyzing a startup, pay close attention to how scrappy and capital efficient they are. Do they have excessively nice office space? Are the founders making too much in salary? Does it seem like the executives are working like animals, or do they have the big company mindset where they take it easy? Startups are nothing like established, revenue-generating compani…

Hahaha. Work like an animal for some guy who is semi-retired. Pass on that deal.

Do you have the money to fund it yourself? Do you have the network you need to greatly increase your chances of success at each stage? If so, definitely take that option. If not, the semi-retired guy isn't semi-retired because he gives his money to people that aren't highly motivated and hungry for success.

Re: Things I wish someone had told me before I started angel investing

#205
post #70

Earlier quoted context omitted.

The YC network effect is the secret sauce. Most YC companies would not even be able to bootstrap if it wasn't for YC alums like AirBnB.

Definitely. For an organization that spent a decade teaching startup the importance of building moats, it's no surprise that they've built their own.

If they hadn't built such a moat it would surely be irony but wouldn't have unusual to do what they preach

Re: Things I wish someone had told me before I started angel investing

#206
post #170

Earlier quoted context omitted.

> Fill us in; why did they fail? That would take a book. Or at least a lot more blog posts.

If there could be a book, then there's enough for a blog post for the four cases you mentioned. As it is, you are telling me that during the night aliens will attack my business, leave without a trace, but have my business in ruins by 8 AM in the morning. Your claim is the first I ever heard of such a thing. Having orders of magnitude better price/performance is amazing. An "order of magnitude" is usually a factor of…

> you are telling me that during the night aliens will attack my business

That's right. That is exactly what I am telling you. Aliens. Definitely aliens.

> Your claim is the first I ever heard of such a thing.

What can I say? You heard it here first.

> Having orders of magnitude better price/performance is amazing.

Yes. It was.

> those are not easy to come by

Indeed not.

> What went wrong?

That's a long story. But the TL;DR is that we underestimated the difficulty of launching new infrastructure.

Here's some background:

http://www.flownet.com/gat/fnlj.html

> You have an attentive audience waiting!

And I also have a lot of other demands on my time.

Re: Things I wish someone had told me before I started angel investing

#207
post #133
post #127

Earlier quoted context omitted.

A $5k check will give a super-early-stage "startup" (two or three college kids) with no salaries and about $1000/month burn rate ("living expenses" in the right market outside of SV) about four months of runway. You'd have to approach at a sufficiently early stage (like so: http://velocity.uwaterloo.ca/funding/velocity-fund/ ).

What share of the company would you expect for that kind of investment? If the amount would be trivial then why would you bother (little reward for so much risk), but if it's non-trivial then why would they accept your money, given how small the amount is compared to the value of their sweat equity? If they really believe in what they're doing, they won't want to give chunks of it away so cheaply. Conversely, if they…

>If they really believe in what they're doing, they won't want to give chunks of it away so cheaply. Conversely, if they're willing to sell on those terms, wouldn't you be concerned that they aren't serious?

If they're college kids or new college hires, you'd probably banking on them not knowing how valuable whatever they're making is.

Re: Things I wish someone had told me before I started angel investing

#208
post #3

My 2 cents - As an investor or potential employee when analyzing a startup, pay close attention to how scrappy and capital efficient they are. Do they have excessively nice office space? Are the founders making too much in salary? Does it seem like the executives are working like animals, or do they have the big company mindset where they take it easy? Startups are nothing like established, revenue-generating compani…

When you see startups blow millions a year on AWS spend because its "easy", when you could do the same on dedicated hardware for 1/10th or even 1/100th the price, it always shocks me. Yes, queue the comments about "Total cost of ownership", past the point where you cant afford an OPs person(s) (which you will eventually need for AWS anyways) AWS is a money-sucking black hole.

I am a huge proponent of self-hosting, but there's other considerations when it comes to doing something like cloud - namely, CAPEX vs OPEX (Capital Expense vs. Operating Expense).

Having your own equipment is a CAPEX and investors don't like to see those on a balance sheet at all due to various accounting reasons. Mostly its seen as a burden. Cloud is an OPEX and investors seem to prefer renting to owning.

Personally I don't understand why spending 3x more is more attractive to investors, but often the technical reason being right is superseded by the business logic.

Re: Things I wish someone had told me before I started angel investing

#209

Every single word in this article burns clear and bright and true. Every word. Every paragraph. Every penny paid for every hard lesson learned. If you want to get into the angel game in 2017, and you want to do it to make money, then I'd sincerely advise you to go take out $5-10k for a weekend in Vegas, and try to get really good at a game of complete chance, like roulette. "Good" at roulette, you're thinking? What c…

Yeah angel investing seems to be a wealthy mans game. You probably need to make at least 10 bets to have a chance at earning your money back. I did a little research and it looks like the first YC batch was comprised of 9 companies. Two of those companies, Reddit and Loopt, likely generated all the returns for that batch.

PG agrees you, he wrote a whole essay about the subject in 2012 [1]. At that point in time, he wrote that "just two companies, Dropbox and Airbnb, account for about three quarters of [YC's value]."

[1] http://www.paulgraham.com/swan.html

Re: Things I wish someone had told me before I started angel investing

#210

Earlier quoted context omitted.

Unless you saw something else, he was making a joke about having his own biases, not that he could identify Zuckerberg due to keen founder detection instincts: > And Graham knew that he had his own biases. “I can be tricked by anyone who looks like Mark Zuckerberg. There was a guy once who we funded who was terrible. I said: ‘How could he be bad? He looks like Zuckerberg!’ ” http://www.paulgraham.com/tricked.html

No, it wasn't that. I don't see it on paulgraham.com. It was probably an HN comment.

You're probably thinking of this interview at startup school: https://youtu.be/MGsalg2f9js (7:40)
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