00:00 – Alan's Current Business Overview

• Running an 8-figure e-commerce operation and launching a trading fund

• Transition from law to entrepreneurship

01:00 – The Early Grind: 80-Hour Weeks & the NYC Commute

• Burnout from legal career

• Starting e-commerce as a side hustle with his wife

03:00 – Scaling Up: From Dropshipping to Stocking Inventory

• Early challenges and rapid pivots

• The move to Texas for logistical optimization

05:00 – Learning to Lead in a Warehouse World

• Leasing space without experience

• Hiring former fulfillment center manager

• Shipping challenges in extreme heat

07:00 – Growth Strategy and Multi-Warehouse Expansion

• Warehouses in Pennsylvania and California

• Remote operations and strategic scaling

08:00 – The COVID Crash: Exhaustion, Supply Chain Chaos & Pressure

• Operating as an essential business during lockdown

• Staff anxiety, childcare gaps, and commitment burnout

10:00 – Alan’s Flex-Time Innovation

• Creating a system where employees schedule themselves

• Boosting productivity by reducing pressure

• Employees seeking raises and returning to stability

13:00 – Middle Management Mayhem

• Alan’s issues with HR and traditional management

• Replacing managers with promoted team members

• Real examples from Walmart and corporate life

17:00 – Remote Work vs Office Life: Alan's First Principles Approach

• Why forcing people back doesn’t always make sense

• Context-based decisions and team needs

• Frustrations with traditional leadership thinking

21:00 – Burnout & Breakdown: The Hidden Mental Health Cost

• Rebuilding a warehouse post-crisis

• Sleeping on-site, nonstop work, and aging overnight

• Cholesterol spikes, hormone crashes, and gas station food

29:00 – Personal Reflection and Hard Boundaries

• Letting go of toxic family

• Ending the “Bank of Alan”

• Finding peace through separation

35:00 – Depression, Doctors & Medication

• Issues with oversimplified diagnoses

• The importance of second opinions

• Nikki shares her own mental health experience

46:00 – Final Thoughts: Change Is Always Possible

• Whether escaping burnout, abuse, or chaos—it’s not hopeless

• Practical advice on changing your environment

• Encouragement to talk, ask for help, and take care of yourself

📋 Full Timestamped Show Notes
[00:00:00] Introduction – Lindsay shares her background as a therapist, speaker, and author.
[00:00:50] Fixing vs. Helping – The “sunny side of control” quote and why our desire to fix things often masks our own anxiety.
[00:03:00] Venting vs. Problem-Solving – Nikki shares her view on venting and being misunderstood when all she wants is to be heard.
[00:04:30] The Pressure Cooker Analogy – Nikki’s take on emotional release and what people really need in the moment.
[00:05:45] Co-Rumination – Lindsay explains how venting can become destructive when it crosses into shared emotional escalation.
[00:07:15] Emotional Support vs. Solutions – The difference between solving the flat tire vs. helping with the stress it causes.
[00:09:00] Nikki's Story: Fear, Safety, and Anxiety – Personal experience of a blowout and how safety matters more than the “fix.”
[00:12:00] Emotional Needs Underneath Situations – Using loneliness or abandonment as core examples hidden beneath surface events.
[00:15:00] Trust, Punctuality, and Respect – Nikki shares how broken trust feels and why being on time is more than a habit.
[00:20:00] Situational Grace vs. Chronic Disrespect – Where to draw the line between understanding and walking away.
[00:24:00] Time Blindness and Boundaries – When mental health becomes an excuse vs. when it needs accommodations.
[00:28:00] Lateness Triggers and Internal Consequences – Lindsay opens up about the unpredictable nature of her own reactions.
[00:32:00] Social Rules and Double Standards – Why we forgive some lateness (like doctors) but not others.
[00:34:00] Late to the Rehearsal Dinner – A story of how chronic lateness can end relationships.
[00:36:00] Respect, Calendars, and Communication – Nikki and Lindsay agree on what it means to take other people’s time seriously.
[00:41:00] Computer Files and Digital Chaos – Nikki shares why she organizes her digital world differently than her physical one.
[00:45:00] Email Habits and Boundaries – Morning, mid-day, and evening email checks to avoid constant distraction.
[00:51:00] Overchecking and the Myth of Staying on Top – When checking email becomes procrastination.
[01:00:00] CRMs, Organization Tools, and Real-World Fixes – Why tech tools can make or break small business systems.
[01:08:00] File Naming Systems and Backup Plans – How Nikki manages client folders, naming conventions, and backups.
[01:14:00] Common Disorganization Traps – Like saving to your desktop or missing important calls due to mislabeling.
[01:20:00] Business Risks of Disorganization – Missed leads, tax errors, broken trust, and operational damage.
[01:26:00] Top Advice: Start Small – Simple steps to start organizing your files, calendar, and systems.
[01:30:00] Final Thoughts – Don’t go big and burn out. Tiny consistent actions will keep your business (and brain) running smoother.

[00:00] Intro – Meet Ashwin Gulati, author of Soul Venture, and his global journey from India to Silicon Valley
[01:30] Ashwin’s personal backstory: early jobs, college in the U.S. and U.K., and what led him to startups
[03:45] From side hustles in Europe to launching his first U.S. company in 1997
[05:20] Why writing Soul Venture wasn’t just a business move—it was deeply personal
[06:50] The cost of vulnerability: publishing a book after decades of privacy
[08:05] Explaining startup culture to solopreneurs—what it really means to “start something big”
[10:00] Freedom vs. fantasy: how startup founders often create 20 bosses instead of one
[11:25] Tips from the trenches – why self-care should be part of your business model
[13:10] Core Dream Team vs. Business Dream Team: the therapists and coaches behind sustainable success
[14:45] Timing: the invisible killer of startups
[16:15] Customers, cashflow, and chaos – hard truths about what breaks a business
[17:10] Solopreneur vs. entrepreneur: defining the difference and pros/cons of each
[19:00] Nikki shares her story: how her accidental business still challenges her daily
[21:30] Burnout, drive, and trauma: what your body knows that your business ignores
[23:40] Why personal growth matters more than perfection in business
[25:10] The hardest kind of startup? Restaurants—and why they fail so often
[27:30] Tech startups vs. hospitality: comparing chaos and complexity
[30:00] Team conflict, expectations, and the reality of startup HR
[33:00] Managing people vs. managing a product—where most founders fall short
[35:10] Ashwin’s first startup: a 1997 research tool that predated Pinterest
[37:00] The dot-com bust, pivoting, and surviving as a founder
[38:30] Music talk – from disco kids to Taylor Swift and staying power in both business and pop culture
[40:30] Closing thoughts – the need for honest conversations in the startup world
[41:15] Where to find Soul Venture and connect with Ashwin