Founders Share Their Scariest Startup Stories

Fear is that unpleasant emotion caused by the belief that something is likely to cause pain. In the life of an entrepreneur, that something is usually their startup. In the spirit of Halloween, we asked these founders to dish on what was the scariest moment so far on their startup journey. Warning: These startup stories are not for the faint of heart. Read At Your Own Risk.

“Our team has two cofounders, and we’re now at about 1000 users! My biggest fear at the start was making the first major investment in developing our site. It was the point of no return. I was taking money that we could have used to buy a family car, or take a pretty extravagant vacation towards a dream. It was a HUGE risk, and I’m so happy to have done it.”  Alym Amlani, Founder of


“We had an entire brand, logo and website developed around the name Vous Vitamin and our IP attorney told us we should not file for the name (we had originally been told to) because he feared it would get translated into its English meaning ‘you’ and then we would not get it. We were devastated and after a few nights without sleep and careful thought and consideration of the pros and cons of filing for it, we decided we would take an informed risk and file. Long story short, we got it! Learned our lesson about taking attorney’s advice with a grain of salt.” Arielle Levitan MD, Co-founder Vous Vitamin LLC.


“I was a senior engineer with Intel Corporation. My job was to travel the world with Chairman Andy Grove, doing technical demonstrations on stage at events, and I was incredibly nervous about speaking on stage. I took a comedy class to get over the fear, and the comedy kind of took off.” Dan Nainan, Comedian and Computer Geek.



“I think my scariest moment, which is more like contemplating, is whether I would shelf one startup for another one. I was debating if I want to finish Datelytics, or create GrindHub instead. From my analysis, consisting of research, focus group and pitch, I decided to move forward with GrindHub, and put Datelytics on the shelf as I can’t be managing so many things at once.” Brandon T. Luong and GrindHub.


“I have been taking risk all my life, but one of my biggest risks was developing a product and quitting my safe job.” David Dodgen, Founder of AquaStorage.


“There is so much at stake when you’re building a startup, scary moments happen all the time. But I think the scariest point has to be at the beginning, when the business was still just an idea. When we were at that point, I questioned every day whether the idea even made sense. And even small negative feedback could feel like the end of the world. Once we started seeing people using the website, most of the big existential concerns went away.” Max Galka Co-founder of Revaluate.


“I’d have to say that hiring the right people and not having enough money are the two scariest parts of my business. As a small business owner if I hire one bad egg it can bring down my business in a major way. If I were a large corporation one bad egg would go unnoticed but I can’t afford to lose a single client because of one nonchalant employee.” Emily LaRusch, Founder of Back Office Betties.



“When hiring a member of your team as a startup it is crucial to make the right choice. It can take months to hire a team member and a few months more to acclimate them. New staff can change the vibe in the office which is important to factor in and hard to gauge in an interview. If a new team member doesn’t work out it causes disruption to the team and loss in productivity which is very costly for a small company. Startups typically don’t have a huge staff, therefore, every member of our team is vital and valued. The hiring process is tremendously time-consuming as most startups don’t have HR. This means you have to juggle that amongst all the other leadership responsibilities.” Krystal Kinney, Brand Strategist at THR33FOLD.


“I started GlobaFone 16 ½ years ago by blowing out my retirement account, paying the taxes and fees and putting the remaining cash in the bank. No safety net, do or die. Receiving an invoice from my attorney that put me upside-down, owing more than had in cash and in receivables.” Louis Altman, Founder of GlobaFone.


“In the very beginning, we underestimated the reach of our initial press release and experienced more website traffic and transactions than our system could handle at that time. Shortly thereafter, we faced a host of securities law compliance issues that altered our trajectory and reshaped our model. ” Chase Tweel, Co-founder of TweelX.



“As a six-time serial entrepreneur, the scariest moment came when I had to choose between my family and my business. It came after 9 months of no revenue and no income, right after an attempt at a friends-and-family round failed to materialize. Our third child was three, and she sat me down and told me I had to shelve the business or our family would collapse.” Michael Sattler, Founder of Splitzee.


“Our scariest moment was when we first started we had all our students booked a month in advance. A week before we were going to start our 1st tour, we received a call from the pool where we were going telling us that they decided not to host our program after all. So we had to find a pool in less than a week. We scrambled and we found one. Ever since then we live and breathe flexibility.” Andrew & Mary Ross, co-founders of Sensory Swim.


“The scariest thing for me was this question: ‘Am I good enough?’ When you work for someone else, there’s always the security that if you don’t know something or need further training, you could have your employer’s grace and assistance. After all, they hired you so they are invested in making sure you are fit for the job through review and training, and often they are the experts that you get to learn from.” Josh Rubin of Creative Cali.


“Hurricane Ivan made landfall just west of Pensacola. Over the next several hours, the storm destroyed everything in its path, from personal property to lives. It was a devastating storm and the aftermath was equally devastating due to the loss of life, property and hope. The economy was crippled and thousands of jobs were lost. At Two Maids & A Mop, we did not reopen our doors for business until two full weeks later. We cleaned two homes that day. It was a scary moment. I had just spent the past 17 months building a business from scratch. Along the way, I invested my entire life savings in order to rescue the business from its humble beginnings. The business meant everything to me. But was I prepared to do it all over again?? Yes, this was definitely a scary moment!” Ron Holt, CEO & Founder Two Maids & A Mop.


“I’ve had many ups and downs in my entrepreneurial journey, but the scariest for me was losing a key employee/manager for the first time after our company started having success. You work so hard and go through so much to get a business off the ground, then once it finds its feet and starts growing you lose an integral member of your team. This person was in charge of an entire department and managed more than 100 remote contractors. Two years had been spent establishing training and protocols and turning this project into an integral part of the business, so naturally there was a slight sense of panic when the manager left for a new job. How far and long would this set us back? How do we get someone up to speed? What happens to the projects that the fill-in person was working on? We did the best we could to keep things running by sliding another manager into that role and helping them learn quickly what they didn’t know.” Rob Bellenfant, CEO of Technology Advice.


“Fundraising is easily the scariest and most stressful thing you do as a startup founder. It is all consuming. People tell you all day long that your shit sucks. They turn you down and it’s no, no, no and you go through hundreds if not more no’s if you get a yes. The issue is, no one person can give you the exact advice on how to do it. You have to do the research and understand who the right investors are (and I don’t mean brand name). It’s all about who is the right partner for you and why, and it’s about having those conversations in a very open and transparent way.” David Mandell, Co-founder and CEO of PivotDesk.



“My business was designed due to the loss of my baby just last year. In my desperate attempt to treasure my short time with him, I designed and developed a way that I could create an online memory keeping Tribute Page for him with his photos, videos, music, life story and pretty much any detail that would allow me to always remember him and his life legacy. Sharing and marketing my project as it is so painful and close to my heart. Fear of rejection when pitching. Fear of others not understanding both the meaning and use of my concept. Fear of not being prepared or knowledgeable enough.”  Ana Rodriguez, Founder of  Tribute Code.


“Deciding to stop a reliable income to give full time to my startup. You have to get your facility support and make sure everyone realizes the need to save and change lifestyles. I was brought in as the CEO of a startup. There, I had to force one of co-founders out and that was tense. How tense? One of them was always carrying a gun in a bag and during a tough negotiations, he kept playing with that bag/gun. Thank goodness the other cofounder was a gentleman!” Alain Briancon, Founder and CEO of Kitchology.


“Starting your own business IS difficult. The scariest moment as a startup that has accelerated very quickly over the past year, is not one moment. It’s a series of moments that feel like you’re about to be pushed off a cliff. No parachute. No one around to witness the horror. No net to catch you. And on top of it, you don’t know how far or how long you will be falling. While you’re falling, you still have to move forward, step-by-step every day, with the team that is counting on you to be the CEO, the team leader.” Arry Yu,  Co-Founder and CEO of GiftStarter.



“One of the scarier moments when we first started ZinePak was going to meet a large corporate client of ours face to face. In today’s day and age you can create and execute entire multi-million dollar programs without ever meeting the person on the other end of an email or conference call. We had spent four months working with this fortune 500 company but had never met them. My co-founder and I were young – 25 and 27 respectively – and we were terrified of meeting them for fear that they would judge us based on our age and gender. While in the end we had a right to be scared (a few older gentlemen in the room were openly horrified by our age and made it a point to say so!) the overall feel of the meeting was definitely less of a trick and more of a treat!” Kim Kaupe, Co-Founder of ZinePak.


“The scariest moment of my entrepreneur career was quitting my full-time job. I had only two years’ work experience after graduating from Griffith University, and I liked my full-time job at Hewlett-Packard. But developing a company after working all day forced me to either take the plunge into entrepreneur uncertainty or put my start-up dreams on hold. I decided to quit and start SaleHoo with only $500 of my own money and $500 of Co-Founder Mark Ling’s money. It took eight months before I started earning a profit, but it was well worth the risk. Today, I’m CEO and co-founder of three companies, and the parent company of which was named the 44th fastest-growing company in New Zealand on the Deloitte/Unlimited Fast 50 index. I can’t imagine my life being any other way.” Simon Slade is CEO and co-founder of Affilorama.


“Seven months after starting the company, we found ourselves in a position where our seed money was drying up and we needed funds to keep the lights on. We had one investor who could fund the company for some time and was very interested, but the clock was ticking and the dangerously close to our “cash out” date. We were able to make one last payroll (with the founding team taking no pay) and walked into our final meeting with the investors knowing that the entire company was on the line. Thankfully, we’ve been blessed with great investors and advisors and we walked away from that meeting with enough funding to keep pursuing our goals.” – Josh Spears, Co-founder of Traitify


Share with us your scariest startup moment.


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Written by:
Camila has been heavily active in South Florida’s tech startup community, where she is a co-host of a local radio show called pFunkcast. Camila previously worked at Greenpeace International and the Organization of the Prohibition of Chemical Weapons (OPCW) in various communication roles. A proud Brazilian who spent most of he life in Peru, she is passionate about traveling and documentaries.
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