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Confidential
How to Know When
It’s Time to Quit
(with Quitter, Elyse Ash)
September 20, 2022
Confidential
Hi, I’m a Quitter!
● Elyse Ash
● Ad industry copywriter + creative director
● “Accidental founder”
● CEO of Fruitful Fertility
Founded with my husband, Brad Ash
● Currently Growth Manager at Cloudburst SBC
● Also a writer, speaker, marketer, IVF mama x2,
storyteller, quitter
Confidential
Fruitful Fertility
● Started in 2016 with my husband from a
personal problem
● Built an app together
● Press! Panels! Glitz! Glam! Fundraising!
● Raised $100K in Friends + Family Round in
February 2020
● Pandemic…
● Tried to sell B2B but couldn’t crack the fertility
clinic code
● Couldn’t find a way to monetize at scale
● Got massively overwhelmed and couldn’t even
Fruitful Fertility
2016 - 2021
Confidential
Warning Signs
Confidential
Confidential
Warning Signs
● You’re running out of money / runway
● You’re consistently not hitting your revenue, user or growth projections…by a lot…
● You don’t seem to have good product market fit
● You cannot raise money even though you’re doing “everything right”
● You’re fantasizing about quitting
● You hate Monday and spend all weekend dreading it
● You’re agitated and anxious pretty much all the time
● You’re burnt out and nothing seems to help
● Your health (physical or mental) is suffering (e.g. stomachaches, can’t sleep)
Confidential
Things to Try First
● Take a vacation, break, sabbatical, anything
● Delegate tasks to other employees or just stop doing certain things that aren’t critical to
the business (whittle down your to-do list)
● Get more support from friends, family members or other founders
● Journal and write about your feelings
● Find a therapist or life coach to work with
● Prioritize your health: get more sleep, find ways to move your body that feel good,
spend more time with family/friends/pets
Confidential
The Sunk Cost Fallacy
“The sunk cost effect is the general tendency for people to continue an
endeavor, or continue consuming or pursuing an option, if they’ve invested time
or money or some resource in it.
That effect becomes a fallacy if it’s pushing you to do things that are making you
unhappy or worse off.”
- Christopher Olivola
Professor of Marketing at Carnegie Mellon’s Tepper School of Business
Confidential
Considerations
Confidential
Considerations
● Legal
○ Can you quit? Do you own your company?
○ Do you have active users who you have promised a service to?
● Personal Finances
○ Will you and your family be ok financially?
○ What do you need financially?
● Could you sell your company or product?
○ Is there interest? What assets do you own? Who do you know or could you be
introduced to who might be interested?
○ Could you sell pieces of your company or product? (Email lists, content or brand
assets like logo, name, web domain)
Confidential
Making the Decision
● Run the math and metrics. Be honest with yourself about how things are really looking.
○ How does your cash flow look?
○ How much runway do you have?
○ How do your projections look?
○ What kind of feedback are you hearing from users/customers?
● Are there parts of your job that you can delegate or simply not do anymore?
● Are you just in a funk?
● What is your gut telling you?
Confidential
Logistics
Confidential
Logistics
● There are different ways to “quit:”
○ Option 1: Step down as CEO and have someone else run the company
○ Option 2: Sell the company (or parts of it)
○ Option 3: Shut it down completely
● Make sure you have an A+ business attorney (and accountant)
○ Account for the costs of closing a business (taxes, legal fees)
● Talk to your family, business partners and attorney (in that order)
● Communications plan:
○ Investors
○ Advisors
○ Employees
○ Users/customers
○ Public (potentially)
Confidential
Selling Assets
● What assets can you sell?
○ Name, logo + brand
○ URL
○ Data
○ App or proprietary tech
○ Email lists
○ IG or other social media accounts
Confidential
Feelings
Confidential
Feelings
● You are going to have BIG feelings
○ You’ll prob feel like crap
○ Then feel relieved
○ Then feel like crap again
● Make space for ALL the feelings and try not to judge them
● Find other founders to talk to who have made this decision
● Create a narrative (both for the company AND for yourself)
○ What happened, why did you close it, what do you want to do next?
● Post-mortem the experience
○ Did you LIKE running your own company?
○ What parts did you enjoy/dread?
○ What would you do differently?
○ Who did you like working with?
Confidential
My Takeaways from Fruitful
● Don’t work with my husband again if I want to stay married
● Find another co-founder equally as invested with a different yet complementary
skill set
● Work on a problem I care about but that is not connected to personal trauma
● No more healthcare. Seriously, never again.
● Don’t be scared to fail. I failed and I lived (and still had fun).
Confidential
Dos + Donts
Confidential
Do:
● Honor your feelings: Relief, guilt, stress, embarrassment, freedom. All real. All valid.
● Remind yourself what really matters
● Take a lil break if you can afford it; I called mine a “sabbatical” and it lasted 6 months
● Make a plan and a timeline
● Keep your mouth shut otherwise
● Talk to other founder friends - especially ones who have done this before and
understand what you’re going through
● Have a firm grasp on your personal finances and know what you need to do next (e.g.
take a break, do consulting work, jump into something full-time)
Confidential
Don’t:
● Make any rash decisions
● Wait until you have zero dollars and zero runway left
● And don’t wait until you are so freakin fried that you can’t even
● Blindside your investors, users and employees
● Overshare with the public (and be careful what you put in writing)
● Blame the company’s failure on external factors
● Judge yourself too harshly
Confidential
Remember:
● GOOD JOB. Whatever you choose to do, you built something. You tried! So few people
do that and it’s important to honor this huge effort.
● You are not trapped. There is always a solution.
● You can still quit even if your company is succeeding.
● You’re not alone. You’re not a failure. I know *so* many other people who went down
this path and realized it wasn’t for them. No shade. No shame.
● Nothing is more important than your health. Physical. Mental. Spiritual.
Confidential
Theodore Roosevelt
“It is not the critic who counts: not the man who points out how the strong man stumbles or
where the doer of deeds could have done better. The credit belongs to the man who is
actually in the arena, whose face is marred by dust and sweat and blood, who strives
valiantly, who errs and comes up short again and again, because there is no effort without
error or shortcoming, but who knows the great enthusiasms, the great devotions, who
spends himself in a worthy cause; who, at the best, knows, in the end, the triumph of high
achievement, and who, at the worst, if he fails, at least he fails while daring greatly, so that
his place shall never be with those cold and timid souls who knew neither victory nor defeat.”
Confidential
Questions?
elyse.ash@cloudburststudio.com

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How to Know When It's Time to Quit

  • 1. Confidential How to Know When It’s Time to Quit (with Quitter, Elyse Ash) September 20, 2022
  • 2. Confidential Hi, I’m a Quitter! ● Elyse Ash ● Ad industry copywriter + creative director ● “Accidental founder” ● CEO of Fruitful Fertility Founded with my husband, Brad Ash ● Currently Growth Manager at Cloudburst SBC ● Also a writer, speaker, marketer, IVF mama x2, storyteller, quitter
  • 3. Confidential Fruitful Fertility ● Started in 2016 with my husband from a personal problem ● Built an app together ● Press! Panels! Glitz! Glam! Fundraising! ● Raised $100K in Friends + Family Round in February 2020 ● Pandemic… ● Tried to sell B2B but couldn’t crack the fertility clinic code ● Couldn’t find a way to monetize at scale ● Got massively overwhelmed and couldn’t even Fruitful Fertility 2016 - 2021
  • 6. Confidential Warning Signs ● You’re running out of money / runway ● You’re consistently not hitting your revenue, user or growth projections…by a lot… ● You don’t seem to have good product market fit ● You cannot raise money even though you’re doing “everything right” ● You’re fantasizing about quitting ● You hate Monday and spend all weekend dreading it ● You’re agitated and anxious pretty much all the time ● You’re burnt out and nothing seems to help ● Your health (physical or mental) is suffering (e.g. stomachaches, can’t sleep)
  • 7. Confidential Things to Try First ● Take a vacation, break, sabbatical, anything ● Delegate tasks to other employees or just stop doing certain things that aren’t critical to the business (whittle down your to-do list) ● Get more support from friends, family members or other founders ● Journal and write about your feelings ● Find a therapist or life coach to work with ● Prioritize your health: get more sleep, find ways to move your body that feel good, spend more time with family/friends/pets
  • 8. Confidential The Sunk Cost Fallacy “The sunk cost effect is the general tendency for people to continue an endeavor, or continue consuming or pursuing an option, if they’ve invested time or money or some resource in it. That effect becomes a fallacy if it’s pushing you to do things that are making you unhappy or worse off.” - Christopher Olivola Professor of Marketing at Carnegie Mellon’s Tepper School of Business
  • 10. Confidential Considerations ● Legal ○ Can you quit? Do you own your company? ○ Do you have active users who you have promised a service to? ● Personal Finances ○ Will you and your family be ok financially? ○ What do you need financially? ● Could you sell your company or product? ○ Is there interest? What assets do you own? Who do you know or could you be introduced to who might be interested? ○ Could you sell pieces of your company or product? (Email lists, content or brand assets like logo, name, web domain)
  • 11. Confidential Making the Decision ● Run the math and metrics. Be honest with yourself about how things are really looking. ○ How does your cash flow look? ○ How much runway do you have? ○ How do your projections look? ○ What kind of feedback are you hearing from users/customers? ● Are there parts of your job that you can delegate or simply not do anymore? ● Are you just in a funk? ● What is your gut telling you?
  • 13. Confidential Logistics ● There are different ways to “quit:” ○ Option 1: Step down as CEO and have someone else run the company ○ Option 2: Sell the company (or parts of it) ○ Option 3: Shut it down completely ● Make sure you have an A+ business attorney (and accountant) ○ Account for the costs of closing a business (taxes, legal fees) ● Talk to your family, business partners and attorney (in that order) ● Communications plan: ○ Investors ○ Advisors ○ Employees ○ Users/customers ○ Public (potentially)
  • 14. Confidential Selling Assets ● What assets can you sell? ○ Name, logo + brand ○ URL ○ Data ○ App or proprietary tech ○ Email lists ○ IG or other social media accounts
  • 16. Confidential Feelings ● You are going to have BIG feelings ○ You’ll prob feel like crap ○ Then feel relieved ○ Then feel like crap again ● Make space for ALL the feelings and try not to judge them ● Find other founders to talk to who have made this decision ● Create a narrative (both for the company AND for yourself) ○ What happened, why did you close it, what do you want to do next? ● Post-mortem the experience ○ Did you LIKE running your own company? ○ What parts did you enjoy/dread? ○ What would you do differently? ○ Who did you like working with?
  • 17. Confidential My Takeaways from Fruitful ● Don’t work with my husband again if I want to stay married ● Find another co-founder equally as invested with a different yet complementary skill set ● Work on a problem I care about but that is not connected to personal trauma ● No more healthcare. Seriously, never again. ● Don’t be scared to fail. I failed and I lived (and still had fun).
  • 19. Confidential Do: ● Honor your feelings: Relief, guilt, stress, embarrassment, freedom. All real. All valid. ● Remind yourself what really matters ● Take a lil break if you can afford it; I called mine a “sabbatical” and it lasted 6 months ● Make a plan and a timeline ● Keep your mouth shut otherwise ● Talk to other founder friends - especially ones who have done this before and understand what you’re going through ● Have a firm grasp on your personal finances and know what you need to do next (e.g. take a break, do consulting work, jump into something full-time)
  • 20. Confidential Don’t: ● Make any rash decisions ● Wait until you have zero dollars and zero runway left ● And don’t wait until you are so freakin fried that you can’t even ● Blindside your investors, users and employees ● Overshare with the public (and be careful what you put in writing) ● Blame the company’s failure on external factors ● Judge yourself too harshly
  • 21. Confidential Remember: ● GOOD JOB. Whatever you choose to do, you built something. You tried! So few people do that and it’s important to honor this huge effort. ● You are not trapped. There is always a solution. ● You can still quit even if your company is succeeding. ● You’re not alone. You’re not a failure. I know *so* many other people who went down this path and realized it wasn’t for them. No shade. No shame. ● Nothing is more important than your health. Physical. Mental. Spiritual.
  • 22. Confidential Theodore Roosevelt “It is not the critic who counts: not the man who points out how the strong man stumbles or where the doer of deeds could have done better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly, who errs and comes up short again and again, because there is no effort without error or shortcoming, but who knows the great enthusiasms, the great devotions, who spends himself in a worthy cause; who, at the best, knows, in the end, the triumph of high achievement, and who, at the worst, if he fails, at least he fails while daring greatly, so that his place shall never be with those cold and timid souls who knew neither victory nor defeat.”