Founders share their most terrifying startup stories


Fear is an unpleasant feeling caused by the belief that something can cause pain. Something in an entrepreneur’s life is often their start. In the spirit of Halloween, we asked these founders to share their scariest moments 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 founders, and now we’re almost 1000 users! My biggest fear in the beginning was making the first big investment in developing our site. It was a point of no return. I was taking money that we could have used to buy a family car or go on a dream vacation. It was a big risk, and I’m so glad I did it. Alim Amalani, founder of

“There was a whole brand, logo and website created under the name Vous Vitamin, and our IP lawyer told us that we shouldn’t register (as we were originally told) because he was afraid that the name wouldn’t be translated into English. ‘And then we wouldn’t get it. I was devastated and after a few sleepless nights and careful thinking. And after considering the pros and cons of filing, we decided to take an informed risk and file. Long story short, we got it! We learned our lesson about taking an attorney’s advice with a grain of salt. Arielle Levitan MD, Co-Founder Vous Vitamins LLC.

“I was a senior engineer at Intel Corporation. My job was to travel the world with Andy Grove, the chairman, 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 started. Dan Nainan, comedian and computer geek.

“I think my scariest moment was not being able to carry one start to another. I was debating whether I wanted to end Datelytics or create GrindHub instead. After my analysis, which included research, focus groups, and pitching, I decided to move forward with GrindHub, and put Datelytics on the shelf because I couldn’t manage too many things at once. Brandon T. Luong and GrindHub.

“I’ve been taking risks all my life, but one of my biggest fears was making a product and quitting my safe job.” David Dodge, founder of AquaStorage.

“There’s so much at stake when you build a startup, scary moments happen all the time. But I think the scariest point should be at the beginning, when the business was still just an idea. While we were in that position, I wondered every day if the idea made sense. And even the slightest bit of negative feedback can feel like the end of the world. Once we started seeing people using the website, most of the big existential concerns disappeared. Max Galka co-founder of Revaluate.

“I have to say that hiring the right people and not getting enough money are the two scariest parts of my job. As a small business owner, if I hire one bad egg, it can seriously hurt my business. If I were a large corporation, one bad egg wouldn’t be known, but I can’t afford to lose a customer because of one non-employee. Emily LaRouche, founder of Back Office Homes

“When hiring your team member as a starter, it’s important to make the right choice. It can take months to hire a team member and a few months to acclimate them. New employees can change the vibe in the office, which is important in interviews and difficult to gauge. If a new team member doesn’t work out, the team will It results in frustration and a very costly loss of productivity for a small company. Startups typically don’t have many employees, so every member of our team is critical and valuable. Most startups don’t have a workforce, so the hiring process is very time-consuming. This means you have to juggle other management responsibilities. Krystal Kinney, Brand Strategist at THR33FOLD.

“I started Globaphone 16 ½ years ago by liquidating my retirement account, paying taxes and fees and putting the remaining money in the bank. No safety net, do or die. Receive a copy of the invoice from my attorney if I owe more than what is paid in cash and receipts. Louis Altman, founder of Globaphone.

“Early on, we limited our press release access and experienced more web traffic and transactions than our system could handle at the time. Shortly thereafter, we encountered a number of securities law compliance issues that changed our direction and changed our model,” said 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. After 9 months of no income and no income, an attempt at a friends-and-family round failed. Our third child was three, and she sat me down and told me I had to take care of the business or our family would fall apart.” Michael Sattler, founder Splits.

“Our scariest moment when we first started was having all our students sign up a month in advance. A week before we were to start our 1st tour, we got a call from the pool we were going to and told us they had decided not to host our program. So we had to get a pool in less than a week. We scattered and found one. Since then, we live and breathe flexibility. Andrew and Mary Ross, co-founders of Sensory.

“The thing that scares me the most is, ‘Am I good enough?’ was the question. When you work for someone else, if you don’t know something or need more training, you always have the safety of your employer’s grace and help. After all, they hired you, so they’re invested in making sure you’re fit for the job through evaluation and training, and they’re the professionals you’ll learn from most of the time. Josh Rubin Creative Cali.

“Hurricane Ivan made landfall west of Pensacola. Over the next several hours, the storm destroyed everything from personal property to lives. It was a severe storm and the results were equally devastating in terms of loss of life, property and hope. The economy has weakened and thousands of jobs have been lost. At Two Maids & A Mop, we haven’t opened our doors for business in two full weeks. We cleaned two houses that day. It was a very scary time. I spent the last 17 months running a business from scratch. Along the way, I invested my entire life savings to save the business from its humble beginnings. The business means everything to me. But was I ready to do it again?? Yes, this was definitely a scary time! ” Ron Holt, CEO and Founder of Two Mids & Mops.

“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 since our company started becoming successful. You work so hard and spend so much to get a business off the ground, then once it finds its footing and starts to grow, you lose a key member of your team. This person is the head of the entire department and manages over 100 remote contractors. It’s been two years of establishing training and protocols and turning this project into an integral part of the business, so naturally there was a bit of trepidation when the manager left for a new job. How far and tall does this set us back? How do we pick someone up quickly? What happens to the projects the recipient has been working on? We did everything we could to keep things moving by having another manager step into that role and help them quickly learn what they didn’t know. Rob Bellenfant, CEO of Technology Consulting.

“Raising money is one of the scariest and most stressful things you do as a startup founder. It is all consuming. People tell you that your pee sucks all day. They will reject and say no, no, no and if they get a yes then hundreds if not more then no no. The problem is that no one can give you the right 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 names). It’s all about who is the right partner for you and why, and making those conversations very clear and transparent. David Mandel, co-founder and CEO of Pivot Desk.

“My business was born out of the loss of my son last year. In an effort to cherish the short time I had with him, I designed a tribute page for him with photos, videos, music, life stories and any detail that would allow me to do the best I could. Always remember him and his legacy. My project is very painful and close to my heart so sharing and marketing it. Fear of rejection while designing. Fear of others not understanding the definition and use of my concept. Fear of not being prepared or not having enough knowledge. Ana Rodriguez, founder of the tax code.

“Deciding to give up a reliable income to devote full time to my startup. You have to get resource support and make sure everyone understands the importance of saving and changing lifestyles. I came as the CEO of a startup. There, I had to force one of the entrepreneurs and that was stressful. How much Is there tension? One of them always carried a gun in a bag and kept playing with that bag/gun during tough negotiations. Thank goodness the other founder was a gentleman!” Alain Briancon, founder and CEO of Kitology.

“Starting your own business is hard. It’s not one single scariest moment, like last year’s fast-paced startup. It’s a series of moments where you feel like you’re about to be pushed off a cliff. A parachute. There’s no one watching the horrors around you. There’s no net to catch you. And on top of that, what? “You don’t know how far and how far you’re going to fall. While you’re falling, you still have to step up every day with a team that sees you as the CEO and team leader.” Ari Yu, co-founder and CEO of GiftStarter.

“One of the scariest moments when we first launched ZinePak was to meet face-to-face with one of our large corporate clients. In this day and age, you can create and execute multi-million dollar programs without having to reach the person on the other end of an email or conference call. We spent four months working with this fortune 500 company but never met. My co-worker and I were young – 25 and 27 respectively – and we were afraid to meet them for fear that they would judge us based on our age and gender. When we finally had the right to be scared (a few seniors in the room were clearly shocked at our age and made it a point to say so!) the overall mood of the meeting was decidedly less witty and more so. Good thing!” Kim Kaupe, co-founder of ZinePak.

“The scariest moment in my entrepreneurial career was quitting my full-time job. After graduating from Griffith University, I had two years of work experience, and I fell in love with my full-time job at Hewlett-Packard. But starting a company after working all day forced me to either go into entrepreneurial limbo or put my startup dream on hold. I decided to start Salehuo with only $500 of my own money and $500 of co-founder Mark Ling’s money. It took eight months before I started making a profit, but the risk was worth it. Today, I am the CEO and co-founder of three companies, and the parent company is the 44th fastest growing company in New Zealand on the Deloitte/Unlimited Fast 50 Index. I can’t imagine my life going any other way. Simon Slade is CEO and Co-Founder of Affilorama.

“Seven months after starting the company, we reached a point where our seed money was drying up and we needed money to keep the lights on. We had one investor who had been funding the company for a while and was very interested, but the clock was running out and it was very close to the “cash out” date. We were able to pay one last salary (without paying the founding team) and went into the final meeting with investors knowing that the entire company was on the line. Thankfully, we’ve been blessed with great investors and mentors and have enough funding to sustain our goals. – Josh Spears, co-founder of Treatise

Share your scariest startup moment with us.


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