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$1.6B in funding and $7B in exits: Chicago tech just had its best year ever

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Re: $1.6B in funding and $7B in exits: Chicago tech just had its best year ever

#72

Chicago has a significant advantage: it's more "normal" in that it's more representative of the United States, than the Bay Area. This provides a fertile ground for new companies to emerge: - Childcare / anything to do with children (e.g. Sittercity) - Things for people without college degrees -- SF has 48% [1] degreed workforce vs. 28% [2] nationally. - People in Chicago/the rest of the US have houses; over 80% of S…

Silicon Valley is somewhat of an aberration at this point. There's an S-curve to concentration (whether in talent, resources, or attention) and while the bulk of American cities are hurting due to a lack of software talent, Silicon Valley is hurting in its own way. It has a lot of engineering talent but a collective lack of political talent (which is what prevents engineers from organizing and getting real equity instead of fucking 1% for the first engineer) and such abysmal HR/management that an exclusionary macho brogrammer culture (that wouldn't fly outside of VC-funded startups) has been allowed to emerge.

So, trying to replicate Silicon Valley isn't a good strategy. It's not very desirable. It's also not possible. Not for New York, not for Chicago, not for Seattle, not for Austin. Should these cities be grabbing a greater share of the new-technology action? Yeah, absolutely. But trying to replicate the culture of a sexist, racist suburban shithole whose high priests think it's OK to block off public beach access (cf. Vinod Khosla) is undesirable. It's happening slowly, but that shit is dying (although it will take two to four decades). Why does the contemporary Valley put such a high premium on pedigree? Because when a society goes into decline, nostalgia dominates. When the Valley was coming up, it didn't matter if you went to Stanford or UC-Irvine or a community college in Nebraska, so long as you were smart and could code. In its decline phase, you see the Stanford Welfare of Clinkle and Snapchat getting funded.

Talent has a natural desire to concentrate, and that might limit us to ~10 strong tech cities in the US, but Silicon Valley has blown past that natural inclination toward concentration. It's deep into the "congested" territory.

What makes Silicon Valley is that it's a condensation point for passive capital. Passive capitalists (teachers' pension funds that invest in VC firms) want returns, and don't seem to strongly care about where or how the capital is deployed. The priesthood that is trusted (in error) to do so are VCs who mostly live in California, and who almost never fund companies more than 30 miles from where they live, so the job and wealth creation is limited to a small geographic area (in which it's almost impossible for an engineer, if he's starting now or recently, to make wealth due to astronomical real estate costs) far away from where the passive capitalists live. Now, if the passive capitalists had a vote, they probably wouldn't want all of their money being directed at a small geographical area where most of them could never afford to live. All being equal-- and by "all", I mostly mean "return on investment"-- Nebraska police officers would rather their pensions be invested in Nebraska businesses and create jobs there... rather than have that money be funneled off to California. Of course, they'd be completely happy to have their money invested in California if that would bring better returns... but VC has been a low-performing asset class for a decade-- the VCs focus on their own careers rather than building great companies or generating returns on the portfolio-- so the passive capitalists are arguably getting screwed. If concentrating the passive capital in Silicon Valley was generating decent returns, then there'd be no reasonable argue against it, but it's not.

This is a long-form way of saying that I agree with you. Replicating Silicon Valley is a backward-looking strategy that won't work in Chicago or New York. These cities, instead, should focus on their own assets. I think Chicago (or Seattle, or Boulder, or for a longer shot, Minneapolis) is a contender for being a different kind of technical leader in, say, 2030... because Chicago has an unusual advantage of a perceived playing-from-behind while actually not being that far behind; that's fairly antithetical to the Valley's Dunning-Kruger smug cloud... but it won't look like the existing Valley. It'll be something different.

Re: $1.6B in funding and $7B in exits: Chicago tech just had its best year ever

#73
post #66
post #48

Earlier quoted context omitted.

I'll offer a hypothesis to explain #1: It's because Chicago's culture is excessively risk averse. There seems to be a tendency to seek permission or acceptance from peers and others before taking a risk (either in business, fashion, life, whatever). This is actually great for bootstrapping, because it keeps you in touch with the real world and immediate customer demand. But it leads to fewer qualified, technical peop…

> It's because Chicago's culture is excessively risk averse I don't know if the culture is that much more risk averse than SF, but rather that the risk calculation is different. There's such a big tech ecosystem out in SF that "failure" as an entrepreneur might mean raising more money for the next project, or failing that BigCos fighting to hire you. Without the same depth of tech infrastructure, the downside risk is…

I would say that the SF failure-is-good culture has good and bad influences from the VCs. They don't care that you failed. They care why you failed. If their evaluation is that you failed in good faith, you get to call it a learning experience and you get an executive position at Google (preferably something with the authority to buy companies, so you can pay them back) or more funding for your next venture. If they judge you to have failed in bad faith, then you're black-balled. So it cuts both ways. It's nice that they'll go to bat for someone they judge to have failed in good faith; it's bad when someone gets blacklisted as having failed in bad faith (or has his successful business taken from him) because he pissed someone off.

Any time you replace objective evaluation of people with subjective holistic evaluations, you get a system that seems more humane and less sharp-cornered, but you also get corruption. It's the question of which is better: sheer cold fairness or sticky warm humanness that can devolve into corruption or even a reputation economy (meaning, "extortion system") if the powerful abuse their roles in the judgment of others.

You can look at it charitably and say that the VCs are doing good by caring more about the reason for failure than the fact of it. Or you can look at it negatively and say that it creates a culture where (a) slimy operators good at creating impressions can play politics and let their companies rot, knowing that their backers will see their failures as "good faith" regardless of the facts, and (b) those with power over the "holistic" element of evaluation evolve into reputation-making and -breaking extortionists. The "right answer" is somewhere between the two.

With Chicago, I think the problem isn't that there's a lack of good jobs for technical people, but that the job-hopper stigma is still very strong in finance (and that's true everywhere; it's not geographical, and the attitude is similar in SF finance). So it's hard for a trader to bounce back if the startup doesn't work.

If hedge funds were willing to hire people with typical startup/tech CVs-- those tend to show the brutally honest behavior of job-hopping (even at 2 years, or 6 months) if one's career is stagnating, rather than sticking around for 5-6 playing the system or slacking like white-collar people are "supposed" to do when passed over, because it's somehow more disloyal to leave than to slack for years-- then people would less afraid to do startups. The fault isn't with Chicago per se. It's with finance and the F500 world and their anachronistic hatred of the "job hopper".

There's a lot that I don't like about California startup culture but I think job hopping is a good thing. If you're ambitious and it's clear that you've been passed over for advancement, it's better for everyone to move on than to stick around and suck out a salary and play against the system for 5+ years because the white-collar world thinks you're "supposed" to show "staying power" or "loyalty".

At any rate, I think you're completely right. I don't think that California is more or less risk averse than the rest of the country, nor do I necessarily think that risk seeking is even a virtue. California entrepreneurs get to look more risk-friendly just because there's such a high frequency managed outcomes (acqui-hires and executive positions made available if the VCs judge you to have failed in good faith) that VC-funded entrepreneurs can count on one. Where it's pernicious is when these founders justify massive equity disparities (compared to the 0.5% that the first engineer gets) because they "took all the risk" when, in fact, most of these VC-funded founders don't take any more risk than any other corporate employee.

Re: $1.6B in funding and $7B in exits: Chicago tech just had its best year ever

#74

Eh, three things really grind me gears about the tech scene in Chicago. 1) Lots of mediocre entrepreneurs that seem to have the same story: - Little to no hard skills. - Probably got an MBA from a good B-school - Did a stint at a consulting firm and is going to outsmart the competition with all the wisdom they gained at Accenture, McKinsey, BCG, Bain, or some big IL firm. - Does NOT have a technical co-founder but is…

I think this will change as prop trading firms wane & consolidate.

They attract the top STEM talent in Chicago and can pay them extremely well through profit sharing. There are a lot of engineers and "Xs who program" (where X ~= trader/researcher) taking home high-six and low-seven figure bonuses at the best groups. The people are usually very entrepreneurial and the firms have a "tech culture" where good code isn't a cost center. Why would guys getting market base, upside that pays yearly or quarterly, and autonomy trade that for $90k and a lottery ticket to build some glad-hander's dream?

Markets are slow and competition is fierce, so I think you will see a lot guys from these Getco-ish firms leaving because the opportunity just isn't there anymore or the firm culture has changed. Most of these people keep a low profile and have cash socked away. Some will end up bootstrapping their own businesses here in Chicago, building them in the image of the firms where they cut their teeth: nimble, revenue-focused, scientific, and sharing success with employees.

Re: $1.6B in funding and $7B in exits: Chicago tech just had its best year ever

#75
post #57
post #48

Earlier quoted context omitted.

I'll offer a hypothesis to explain #1: It's because Chicago's culture is excessively risk averse. There seems to be a tendency to seek permission or acceptance from peers and others before taking a risk (either in business, fashion, life, whatever). This is actually great for bootstrapping, because it keeps you in touch with the real world and immediate customer demand. But it leads to fewer qualified, technical peop…

>It's because Chicago's culture is excessively risk averse. There seems to be a tendency to seek permission or acceptance from peers and others before taking a risk (either in business, fashion, life, whatever). Absolutely. Many of the early startups were based on needs that could serve people and corporate partners. We don't have a lot of app based businesses.

Are you implying that's a bad thing? Maybe if you want to go public with some insane P/E ratio selling the dream, but B2B tech businesses serve the economy, provide useful jobs, and have staying power.

Re: $1.6B in funding and $7B in exits: Chicago tech just had its best year ever

#76

Eh, three things really grind me gears about the tech scene in Chicago. 1) Lots of mediocre entrepreneurs that seem to have the same story: - Little to no hard skills. - Probably got an MBA from a good B-school - Did a stint at a consulting firm and is going to outsmart the competition with all the wisdom they gained at Accenture, McKinsey, BCG, Bain, or some big IL firm. - Does NOT have a technical co-founder but is…

> I know these people exist everywhere today but there's an unusually large number concentrated in Chicago. Must be something in the water? Finance is also an extremely tempting lure. The pay is quite good (e.g., significantly better than Google), the hours are better, and the firms are generally supportive of external work. Many of the finance firms my friends work at (I've lived in the Chicago area most of my life)…

To add to that, finance in Chicago is very different than finance at big banks. Many of the big players are tech companies first and foremost. Engineers are often on the "money side" of the business and respected/rewarded as such.

Anyone trying to attract talented STEM employees in Chicago should read these to see what they're up against:

http://www.nancyhua.com/2012/12/11/the-and-my-future/

http://qr.ae/3MPL1

Re: $1.6B in funding and $7B in exits: Chicago tech just had its best year ever

#77
post #66

Earlier quoted context omitted.

> It's because Chicago's culture is excessively risk averse I don't know if the culture is that much more risk averse than SF, but rather that the risk calculation is different. There's such a big tech ecosystem out in SF that "failure" as an entrepreneur might mean raising more money for the next project, or failing that BigCos fighting to hire you. Without the same depth of tech infrastructure, the downside risk is…

I would say that the SF failure-is-good culture has good and bad influences from the VCs. They don't care that you failed. They care why you failed. If their evaluation is that you failed in good faith, you get to call it a learning experience and you get an executive position at Google (preferably something with the authority to buy companies, so you can pay them back) or more funding for your next venture. If they…

Traders don't want to hire job hoppers because it's a negative signal about their abilities and ethics. First, if this guy is really so great, why has he flamed out of 3 firms in 5 years? Either he's lying or has some serious personality defect. Second, do I really want a guy who's bounced from firm-to-firm glomming up ideas and IP? Won't he do the same thing to me?

Going away to do a startup doesn't send the same signal. I'd gladly hire someone who did that.

Re: $1.6B in funding and $7B in exits: Chicago tech just had its best year ever

#78

Earlier quoted context omitted.

I would say that the SF failure-is-good culture has good and bad influences from the VCs. They don't care that you failed. They care why you failed. If their evaluation is that you failed in good faith, you get to call it a learning experience and you get an executive position at Google (preferably something with the authority to buy companies, so you can pay them back) or more funding for your next venture. If they…

Traders don't want to hire job hoppers because it's a negative signal about their abilities and ethics. First, if this guy is really so great, why has he flamed out of 3 firms in 5 years? Either he's lying or has some serious personality defect. Second, do I really want a guy who's bounced from firm-to-firm glomming up ideas and IP? Won't he do the same thing to me? Going away to do a startup doesn't send the same si…

Traders don't want to hire job hoppers because it's a negative signal about their abilities and ethics.

You're wrong. I can make the same argument against people with long tenures. Some people, when they realize that they've been passed over for a promotion or that they're not being groomed for the role they want in the future, bounce (external promotion). That's the honest thing to do. Others stick around, play politics, work the system, slack, and wait for others to fail so they can capitalize on the chaos and move up the ranks. In other words, one could make the argument that the able, confident, ethical, honest people job hop and the political actors stick around and climb the ladder.

I don't actually believe that most people with long tenures are unethical. I'd put the correlation right around zero, to be honest about the whole thing. I think that there are patterns that cause good people to have long tenures and bad people to have short ones, and also patterns that cause good people to have short tenures and bad people to have long ones.

First, if this guy is really so great, why has he flamed out of 3 firms in 5 years?

Maybe he's technically excellent but bad at playing the politics. Perhaps he's an overperformer, like McNulty on The Wire. Maybe he's just unlucky. Maybe he didn't flame out, but each move was a major promotion that he wouldn't have been able to get internally.

Second, do I really want a guy who's bounced from firm-to-firm glomming up ideas and IP? Won't he do the same thing to me?

The problem isn't "job hoppers". It's attrition. When people leave, it's disruptive (and the internal disruption to your own processes is so much more of a threat than IP leakage, unless someone's actually stealing code and then it goes to the courts, that the latter is a rounding error). You can control attrition by treating people well and making sure that ambitious people have appropriate opportunities get promoted on time. It has little to do with the people you hire, and much more to do with how you manage them.

The anti-"job hopper" sentiment isn't really about IP. It's about being mean-spirited, and the IP justification is just made to back-fill an already-formed prejudice.

Re: $1.6B in funding and $7B in exits: Chicago tech just had its best year ever

#79

Earlier quoted context omitted.

Illinois, Purdue, Wisconsin, Northwestern and to a lesser extent Michigan dump tons of engineers into Chicago.

Yes although arguably dumps just as many into the valley and NYC

And outside of that, there's a big loss due to proximity. Northwestern hasn't had nearly the impact on tech as Stanford or Cal, and UIUC's biggest alums are in the valley.

Re: $1.6B in funding and $7B in exits: Chicago tech just had its best year ever

#80

Chicago has a significant advantage: it's more "normal" in that it's more representative of the United States, than the Bay Area. This provides a fertile ground for new companies to emerge: - Childcare / anything to do with children (e.g. Sittercity) - Things for people without college degrees -- SF has 48% [1] degreed workforce vs. 28% [2] nationally. - People in Chicago/the rest of the US have houses; over 80% of S…

Silicon Valley is somewhat of an aberration at this point. There's an S-curve to concentration (whether in talent, resources, or attention) and while the bulk of American cities are hurting due to a lack of software talent, Silicon Valley is hurting in its own way. It has a lot of engineering talent but a collective lack of political talent (which is what prevents engineers from organizing and getting real equity ins…

Let's say Chicago (or Seattle, or New York) become tech hubs comparable to Silicon Valley. What's stopping the same bro culture from developing there?

Isn't the misogynistic bro culture a function of a sheltered, narrow upbringing and a nationwide cultural infatuation with "apps" (which only the talented, sought-after Software Engineers can provide)?

From my experience, the bros come from all across the US and Canada, and not just the San Francisco Bay Area. I've lived and worked here all my life, and most people in the tech industry actually moved here from other states. So what's to say they all won't move to Chicago as well?

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