There were a few tricky situations to debug.
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A person with a new, immature manager: mitigations include proactive wide-communication of impact, schedule every six week performance review of 2-3 strengths to double down on and 2-3 areas of weakness to improve, and skip-level meetings.
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A person suffering from anxiety related to engineering interviewing: mitigations include interviewing at companies you don’t want first, bribe a friend to interview you, teach something to someone else on a whiteboard, and tell the interviewer you're nervous but excited and why!
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A few Stripe-related things: a startup asking about PSD2, two operations and business development candidates (both from Nigeria), an internship for a college student for Stripe Atlas (she has very relevant VC internship experience), and 3 engineers and 2 PMs now interviewing.
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There were a few startups trying to get off the ground.
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A college only craigslist in a fancy mobile app (nice demo but no traction, yet!) looking for a technical founder: mitigations include getting as much traction as possible before an app and to hang out where technical people hang out (throw a meetup, etc). Force the serendipity.
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Many reminders that in all cases, the highest likelihood path to a successful company is getting to 100 *paying* customers that love your product (like they scream at you when it's down). Do you have that yet? If not, do anything possible to get there.
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You have to make sure there are paying customers (for B2B), the biggest mistake I made is running a company that had users/traction but when it came time to pay... the users weren't really interested as much as I thought their usage would suggest. Charge early, charge often.
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Have you found 100 users who are falling over themselves to use this service? Is anyone paying? What happens when you double your price?
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Funky one: a Bitcoin payments company reached out looking for potential acquirers. The top issue was their deck offered like 20 value propositions but I fear that puts too much burden on a potential acquirer to create a vision for why to buy this product (the company).
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A “Shopify for freelancers” with a big vision, good team and great founder story but too many features and next feature fallacy.
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My absolute favorite was the woman from Minnesota working on turning her family restaurant’s delicious homemade enchiladas into a frozen food brand. I’m expecting freeze dried enchiladas in the mail soon.
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I helped structure a bunch of job searches. Frequent advice: flip the table over. Find a reason the company will have to reach out to you or how to get your application forwarded to the hiring manager directly rather than in the pile of resumes.
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Build something online to show for yourself other than the resume. Write things online that showcase clear thinking (blog post on what you built or on some other deeply technical topic).
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Make any weird connection in the world to anyone at the company. Imagine you already work there, what things would you have to think about and be responsible for? Then write about that online or give product feedback.
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Resume reviews: My most important message is to use your own voice in your writing: http://www.paulgraham.com/talk.html . There were so many phrases I can't imagine people would say to a close friend. So stilted. I want the resume from your voice.
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Practice writing as frequently as you can. Send a weekly update email with what you did last week, what you're going to accomplish this week, what you've learned, etc.
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