Christine Song: Founders Are Lonelier Than Anyone Admits

Christine Song spent 20 years in HR, the last 10 as the right hand to startup founders, where every problem in the company became her problem. She worked every weekend, answered Slack in the Disney World line, watched three of her founders get removed by the boards that funded them, and never got the exit she was promised. So last year she burned the boats and launched 5to9 Society: a vetted, confidential dinner community for founders and operating leaders, now 60 members across Toronto, Montreal, Ottawa and Vancouver.

We talk about what founders actually say behind closed doors, why your executives won't tell you the truth (you can fire them), why she reference-checks every member with their former CEO, how posting the unglamorous side of HR on LinkedIn meant she never applied for a job again, and why she gives herself 10 years before judging whether this worked.

Chapters
00:00 Cold open
00:22 "Entrepreneurship is no joke": the hard-knocks conversation
01:54 Ten years in corporate, ten years in startups
03:41 Why people join startups, and what happens when the exit never comes
04:42 Growing up in her parents' grocery stores
06:05 The equity carrot
07:11 Slack messages in the Disney World line
09:19 Who should (and shouldn't) become an entrepreneur
11:55 "Do you know how hard it is to make $1?"
14:04 The middle-child theory of entrepreneurs
15:54 Turning down a CEO seat to build what she's good at
16:30 Why 10 years, not 12 months
17:14 The secret society that inspired 5to9
18:18 It's lonely at the top: what founders say behind closed doors
19:23 Twelve people, a private room, Chatham House rules
20:47 How chapters, fireside chats and masterminds work
22:27 Reference-checking members with their former CEO
24:52 Your reputation is your social capital
25:53 Putting yourself out there: how we met
26:53 Ten years of posting the real side of HR on LinkedIn
29:35 The hard conversations you can't have online
30:31 Watching three founders get removed by their own boards
31:56 The CEO who didn't want to go to the party
33:15 What COVID did to community
35:10 Why founder networks tell you what you want to hear
38:21 Where the name 5to9 comes from
40:04 "Don't expect your manager to invest in you"
41:35 The chip on your shoulder
42:30 The performance review that pushed her out of corporate
44:31 Build in Canada or leave for the US?
46:59 Who the community is for
49:01 The business model: dinners, community, referrals, masterminds
52:00 Why she turns people away
53:18 LinkedIn is "we," Instagram is polished you, TikTok is the real you
56:07 There are more founders on TikTok than LinkedIn
58:22 Posting three times a day for a year
59:10 Cold-messaging a billionaire to come to dinner
1:02:13 AI bots are ruining founders' reputations
1:03:43 The room where every hand went down
1:05:31 Reflecting on year one
1:07:03 The sticky note

Connect with Christine
5to9 Society: 5to9society.com/
LinkedIn: linkedin.com/company/5-to-9-society/
Instagram: instagram.com/5to9society/

Get in Touch
Website: laidoffto8figures.com
Instagram: @davidrdinardo / @laidoffto8figures

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