100 days. As many asks as you dare. Loot drops for the brave.
Join the QuestYou know that email you've been drafting and deleting for three weeks? The pitch you rehearsed in the shower but never sent? The opportunity you talked yourself out of before you even tried?
Send it. Submit it. Say it out loud. Then come back here and show us the receipt.
The #AskAnyways Quest is a 100-day community challenge for anyone who's ever let fear of rejection keep them from asking for what they want. Every ask you make — every pitch, application, cold email, bold request — earns you loot. Real, physical, handmade loot from the workshop of a guy who's spent 20 years building things for people who dream big.
This isn't about getting a "yes." It's about proving that "no" won't kill you.
Apply for the thing. Pitch the idea. Send the message. It has to be personalized and specific — no mass blasts, no automated applications. It has to take guts.
Come back here and submit your proof. A screenshot, a confirmation email, a photo — anything that shows you actually did it. Redact whatever you need to.
Your submissions are tracked automatically. Hit a milestone, earn a reward. No random drawings, no algorithms. You earn it, you get it.
A digital #AskAnyways badge and a printable Quest Log to track your journey. Everyone starts somewhere.
An #AskAnyways sticker pack shows up in your mailbox. Put it on your laptop, your water bottle, your bathroom mirror — wherever you need the reminder.
A custom iron-on transfer — put it on anything — plus a handmade item from the Barkeep's workshop. Twenty years of building one-of-a-kind things, and now one of them has your name on it.
A blind box from the workshop. You won't know what's inside until you open it. Every box is different. What you get is between you and the Barkeep.
A custom piece from the Barkeep's workshop, personalized and one-of-a-kind. Fifty asks earned you something nobody else will ever have.
A significant handmade prize, plus a one-hour video call with the Barkeep himself — a private bar chat to talk about your journey, your business, your creative work, whatever you need. Everyone who reaches Mythic gets the call. No exceptions.
Every tier is earned. Not drawn. Not random. Yours. Loot is cumulative — if you reach Mythic, you've earned everything from Common through Mythic.
Still going after 100 asks? Every submission beyond Mythic enters you into the Grand Prize Pool. The grand prize will be revealed during the quest and drawn at the end. The more you ask, the more entries you earn.
One ask, one submission. Show us the receipt and earn your loot.