Hacking your founder psychology to do uncomfortable outreach

Executive overview

Most founders resist asking for help, endorsements, or attention — it feels transactional, not relational. Dr. Sheri Walling, a psychologist and entrepreneur, launched her grief memoir Touching Two Worlds and had to run a full sales and marketing process she found deeply uncomfortable.

The reframe that unlocked it: ask on behalf of the work, not on behalf of yourself.

When you believe the thing you're selling genuinely helps people, you're not selling — you're telling the truth.

Reframing cold outreach

• Asking for favors on your own behalf feels uncomfortable; asking on behalf of the work feels honest
• If you can say "I think this is genuinely important, will you take a look?" with integrity, the discomfort drops
• Rob's parallel: "I'm not selling. I'm just telling my truth." — works when you believe in the product
• Outreach is hardest for relational people who find transactional conversations unnatural

The book launch system

• Built a spreadsheet of every podcast and professional contact worth reaching out to
• For each contact: noted the connection to the work, and what to ask for (endorsement, review, buy, intro)
• Prioritised with a launch consultant (Elizabeth Marshall) — not trying to reach everyone, only the most accessible
• Spent at least one hour per day on outreach, plus time managing responses
• Launched with an unusual event: a live circus show that told the story of the book, giving people an experience rather than a pitch

The hard reality of pitching grief

• Grief is not a "sexy" topic — it won't 10x a business or help someone scale
• Entrepreneurs tend to push vulnerable realities aside in favour of what they can accomplish
• Even supportive allies (Andrew Warner, Channing at IndieHackers) couldn't make the topic fit their audiences
• The honest response from gatekeepers: "We believe in you, but this doesn't fit our audience right now"
• No clever marketing workaround was found — Sheri took people at their word

What's in Touching Two Worlds

• Memoir structured as short essays, each followed by psychological analysis and practical tools
• Sheri lost her father (esophageal cancer) and brother (suicide) within a short period
• Includes journaling practices, breathing exercises, letter-writing — tactical tools embedded in personal story
• Tone alternates between humour and heartbreak; written to be readable independently of personal loss
• Available as paperback, Kindle, and audiobook (read by the author)

Grief and entrepreneurship

• Entrepreneurs experience both high highs and low lows — grief lives naturally in that space
• Grief is present in selling a company, firing someone, having a co-founder leave, watching something you built implode
• Fear of entering grief comes from not knowing how to navigate it — but avoiding it prevents full flourishing
• The title "Touching Two Worlds" reflects the duality: simultaneous darkness and joy, both real at once
• Entering the shadow is the only way to fully experience the lightness on the other side