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Share Your Startup Story

Choose any of the questions below and record your answer. We’ll post your responses and tag your company and personal profiles, giving your insights the visibility they deserve. Please   no pitches, just your genuine stories and insights.

Question Categories:

What’s your origin story as an startup founder and/or leader?

Who was your childhood hero, and how did they influence your career path?

What’s a skill you developed in childhood that unexpectedly helps you as an entrepreneur?

What’s the most unconventional job you’ve had, and how does it relate to your current role?

If you could go back in time and give your younger self one piece of advice, what would it be?

What’s the biggest risk you’ve taken in your career, and how did it pan out?

Describe a moment when you seriously considered quitting. What kept you going?

If your life was a movie, what would be the title of this current chapter?

What’s the most valuable lesson you learned from a failure?

Who’s the most unexpected mentor you’ve had in your career?

Describe your company culture in three emojis.

What’s the quirkiest tradition your team has?

Who’s your work bestie, and why do you click?

What’s the most hilarious mistake you’ve made at work, and how did you recover?

If your company was a character in a TV show, who would it be and why?

What’s the most unusual skill someone on your team has that’s surprisingly useful?

Describe your leadership style using a movie character.

What’s the most creative way you’ve solved a disagreement within your team?

If your company had a theme song, what would it be?

What’s the best idea that came from an unexpected source in your company?

What’s your go-to productivity hack?

Describe your ideal workday in 5 words.

Coffee or tea? And what’s your favorite local spot to grab it?

What’s your favorite “work from anywhere” spot in the city?

If you could swap jobs with any other founder for a day, who would it be and why?

What’s your secret for maintaining work-life balance (or do you think it’s a myth)?

Describe your perfect “mental health day” when you need to recharge.

What’s the most unusual place you’ve ever taken a business call?

If you had to give up your smartphone or your laptop, which would you choose and why?

What’s your go-to stress relief activity during a tough week?

What industry buzzword makes you cringe, and why?

What’s a trend everyone thinks is dying, but you believe is just getting started?

If you had a crystal ball, what would you predict for your industry in the next 5 years?

What’s the most exciting emerging technology in your field?

If you could instantly become an expert in one area outside your current expertise, what would it be and why?

What’s a common misconception about your industry that you’d like to debunk?

Describe a pivot in your industry that caught you by surprise.

What’s an unsexy but crucial aspect of your industry that deserves more attention?

If you could bring back one “dead” technology or practice in your industry, what would it be?

What’s a skill that’s currently undervalued in your industry but will be crucial in the future?

What’s the best thing about building a startup in your city?

If your city’s startup scene was a high school clique, which one would it be?

What’s one thing other startup hubs could learn from your city?

Who’s the unsung hero in your local startup community?

If you could magically change one thing about your city’s business environment, what would it be?

Describe your city’s startup ecosystem in a hashtag or one word.

What’s the most underrated resource for startups in your area?

If your city’s startup scene was a sports team, what position would you play?

What’s a local challenge that’s spawned innovative solutions from startups?

What’s a local challenge that’s spawned innovative solutions from startups?

What’s the toughest decision you’ve had to make as a leader?

Describe a major setback you’ve faced and how you bounced back.

What’s a skill you never thought you’d need, but now use all the time?

How do you handle self-doubt on tough days?

What’s the best piece of criticism you’ve ever received?

Describe a time when you had to completely rethink your business model.

What’s your strategy for making difficult decisions under pressure?

How do you approach giving constructive feedback to team members?

What’s been your biggest challenge in scaling your business, and how are you tackling it?

Describe a time when you had to admit you were wrong. How did you handle it?

If your startup was a flavor of ice cream, what would it be?

What’s the weirdest item in your office?

If you could have any superpower to help run your business, what would it be?

What’s your go-to karaoke song after closing a big deal?

If your company was a meme, which one would it be?

What’s the strangest skill on your resume?

If your startup journey was a reality TV show, what would be its tagline?

What’s the most unusual interview question you’ve ever asked or been asked?

If you could choose any fictional character to join your board, who would it be and why?

What’s the most ridiculous expense you’ve ever tried to write off?

What wild dream for your company keeps you up at night (in a good way)?

If you could instantly solve one global problem with your product/service, what would it be?

If you could collaborate with any company in the world, who would it be and on what?

What’s your “I’ve made it” moment going to look like?

What’s a milestone you’re dying to hit in the next year?

What’s your “I’ve made it” moment going to look like?

If you had unlimited resources, what moonshot project would you pursue?

What’s a future trend you’re preparing for that others might not see coming?

How do you balance short-term gains with long-term vision in your decision-making?

If you could fast-forward 20 years, what do you hope your legacy will be?

What’s the best advice you’ve ever ignored, and why?

If you could put one message on a billboard for all entrepreneurs to see, what would it be?

What’s a common piece of startup advice you think is total BS?

If you could make every aspiring entrepreneur read one book, which would it be?

What’s the most valuable lesson you’ve learned from a competitor?

What’s one thing you wish you’d known before starting your business?

Describe your biggest “aha” moment as an entrepreneur.

What’s a piece of unconventional wisdom you swear by?

If you could go back and change one decision in your entrepreneurial journey, what would it be?

What’s the worst advice you’ve ever received, and how did you realize it was bad?

Describe your networking style in a movie title.

What’s the most unexpected place you’ve made a valuable business connection?

If you could have dinner with three people (alive or dead) to discuss your business, who would they be?

What’s your secret weapon for breaking the ice at networking events?

How do you give back to your startup community, and why is it important to you?

What’s the most creative way you’ve ever followed up after a networking event?

If you could create a new networking event format, what would it look like?

How do you maintain relationships with mentors and advisors?

What’s your approach to building a personal brand alongside your company’s brand?

How do you leverage social media for business connections without losing authenticity?

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