Reflect After, Not Before (Notes from Oct 28 - Nov 3, 2019)

I was a madman and finished through StartUp Podcast and their Gimlet story during the week of these notes. Pretty cool to hear a play-by-play for what was going through their thoughts, especially when they're simple questions but hold such a vital block until the next challenge. It's comforting, as well, that many people go through this. It truly doesn't matter the size of a company or the hoopla associated at the start, there is a huge weight on the shoulders of first-time entrepreneurs coming from full-time employment. Even with the best managers or people in their roles, there are so many things that go into building - and it's always changing.Thankfully, there is an increasing amount of resources now to help you. A large number of people who have scratched the entrepreneur itch have produced reflections, notes and strategies to succeed/fail/avoid mistakes - all through the eyes of those who have succeeded marvelously, exited, failed spectacularly or even quietly. We're lucky that we're in this time, now, simply for the reason that all it takes to DO is just that - ACTION, DO. No longer is there a lack of playbook for the particular road to the madness. More tools, more options and it's whatever you decide to go with. So, the biggest problem is probably now analysis paralysis. Want to make an educated guess as to what may work BEST, but it's hard to know that. Experiment where you can and take leaps everywhere else.I should take more of my own advice, and I'm glad I heard a few podcasts that push me further into this train of thought. The ideas will eat at you until you do it. Don't want to regret inaction - hard to regret action since it'll be what you did and how you took that path. Hope you all enjoy the notes / podcast in each of these paths.

• Jeff Seibert (@jeffseibert), Sr Director of Product at Twitter (20min VC FF032)

• Former founder of Crashlytics, 2011 with Wayne Chang for 300mil users worldwide Acquired by Twitter in 2013 for $259mn
• Cofounded Increo in 2007 and served as COO and lead architect until acquisition by Box in 2009
• Build, share and innovate on their ideas - idea-sharing (doc-sharing, feedback, collaboration)
• Had raised seed $500k in early 2008 - thought it would last about 18 months - for 2009 start, had 6 months to raise Investors were pulling back, taking meetings but not investing - met with 34 / 36 firms on Sand Hill (says it was too much)
• Grew up in Maryland, got Mac for Dummies and had visual application where he changed "Hello, World" to orange color Went to Stanford for college, wanted to think about startups so started group
• Transparency - full may be healthiest culture but it's crazy high, crazy low (so CEOs should moderate) - entire team through cycle is actual stress Productivity can dip if whole team feels this - at Increo it was very transparent Acquisition discussions meant they had 2 months of not being productive - founder has to swallow the ups and downs Box - still was furthering the mission for the acquisition - they had tons of documents and could provide lots of value
• For Twitter acquisition - their executive team had a deeply nuanced view of the mobile ecosystem
• With one of largest apps, had tons of connections, users, and feedback - lead them to have a good scale and vision for the next few years Mobile developers and could succeed in that environment - could provide Crashlytics to grow team and build out products
• Twitter was acquiring 2 companies a month - total transparency of motivations for acquisition and why they were in plans Why was it being considered by company - couldn't guarantee technology, headcount but they were open He moved out to SF because they wanted rep for the company
• For Crashlytics - he took both coast moneys - Flybridge (Jeff Musbridge who suggested a question for how he met cofounder)
• Wayne Chang - few big startup events that people go to - friend had invited Jeff, was talking about side projects - agreed to meet later
• He had a very deep understanding of the technology and intuition for mobile developers
• Gave him a list 3 weeks later out of the blue with mobile apps, their lead, interview notes for feedback and commitment to use beta
• Executes like crazy - fantastic relationship
• Thought they were set up for success when they were acquired and reporting to VP of Eng - didn't anticipate that they had a re-org May put you on other location, lose some activity - should have been a "we want 6-9 months to report / integrate"
• Goal for Crashlytics was to solve mobile bugs/crashes - 100s of millions of devices, 10s of k's of customers
• Could leverage Twitter name and offer the product for free - so instead of doing freemium and enterprise, they could do free everyone
• Total distribution - it was the perfect opportunity - now have 1billion devices
• Have entire team (save for 1) and it has tripled
• He spent 2 years after deal leading developer's platform (all over world on Twitter's services) before moving to consumer product (BlueBird, Twitter app)
• Daring Fireball (Apple fanatic) for favorite blog, career highlight was speaking at Stanford (one of student coordinators originally for Entrepreneurship)
• Acquihires - not a fan for startup perspective, but understands from other side
• Gimlet 8: Our New Show (StartUp Podcast 11/22/14)

• Hiring new people that could be superstars - TLDR hosts WNYC
• Offering lower salary than before but a revenue sharing - "incapable of feeling joy, has had an anxiety stomach ache for the past 5 days"
• They had a bunch of questions: Editorial/managerial relationship (bosses), ad spots for numbers, CPM rate, $ for ongoing web support, logo Had gone through budget stuff initially - PJ & Alex had been part of a union, stability - 6 months later - can they get a commitment?
• Tough to give security if they don't have the security - 4 year vesting plan
• Gimlet 9: We Made a Mistake (StartUp Podcast 12/6/14)
• Uploading first episode of Reply All - new podcast show
• Making a terrible mistake of not clarifying an ad intention for "This American Life" for a son's Minecraft website for Squarespace
• Having a discussion with Ryan's (son) of Laura, who eventually came on to talk with Alex about how she'd felt and interpreted
• Establishing processes and policies for the advertisements
• Gimlet 10: Mixing Art and Business (StartUp podcast 12/22/14)
• Not wanting to add to spending part of business (75% pay cut for Alex)
• 3 months of initial episode of StartUp, 1 month for ReplyAll, and 8 employees in an office with salaries/benefits and advertisements
• Brought in old spreadsheet for month to month project
• Miscalculated the audience numbers - said they'd have 20k listeners after 4 months and they're at 10x that
• Plan was to have 3 shows and then spend a year to build audience
• That plan is gone for audience numbers-wise, but to do another show would cost more money
• Ramping up spending is scary if the audience didn't continue to grow
• Talked to their first hire, Caitlin, producer and her knowing and shouldering a lot of the anxiety
• Nick Craig (@nickcraig1), author of Leading From Purpose (Wharton XM)

• Love as part of purpose statement when he was with West Point staff
• Love of family, country, service
• Where service meets purpose
• Purpose is what everyone can take between business and personal Most people are smart but asked, as fish, to climb a tree (Einstein)
• Ben & Jerry's turnaround - schweaty balls flavor - M&A / movement guy that stayed at B&J's Doubled revenue to $1 bn from 2011-2019
• Level of uncertainty has risen for almost every company
• Used automotive example - what are we going to be selling, buying
• Banks
• Timelines are shrinking
• Talking to Bryn Abraham - love to figure out her purpose
• Figured it out, then she says she wants to write the foreword for your book (what book - his response)
• Set him up with her agent (Ariana Huffington and Peter Schultz's), who had taken his Wharton class
• The agent told him she'd represent him for his book