1. What were you doing before you launched your startup?

I started building my first company right after college. Having attended Carnegie Mellon, my closest friends took high-paying and prestigious jobs at companies like Apple, Google, Facebook, JP Morgan, etc., but I knew from the get go that this wasn’t for me. Both my parents were immigrants that successfully built companies and pulled themselves up by their bootstraps, and I knew from an early age that this was the path I wanted to pursue.

2. When did you realize you wanted to be an entrepreneur?

I was eleven the first time I realized that I wanted to be an entrepreneur. We were living in South America at the time, and my parent’s business was going through a downturn. Naturally, they tried to protect my brother and me from being exposed but found little success in doing so. It quickly became the only topic of conversation at the dinner table and ignited a passion for problem-solving and decision making that has guided me to this day. I found it exhilarating how against all odds, my parents maneuvered their way around a crisis and the resilience it took to do so. I spent the next decade observing my parents build multiple businesses in the US, providing constant reminders along the way that this was the path I wanted to follow.

3. What initial hesitations did you have about starting your first company?

I knew that I was leaving a lot on the table by not starting my career at a big company where I could learn how things operated at scale without the chaos and uncertainty that a startup brings. Ultimately, the pull of starting a company was too big, and I jumped into it with minimal hesitation.

4. What are you doing now?

I’m a co-founder and CEO at Logixboard, a company building the next generation SaaS platform for the two-trillion dollar freight forwarding industry. We relocated the company from Miami to Seattle last year after raising a seed round from some of the top investors in California, Boston, and the PNW.

5. Looking back on your experience of founding a company, what do you know that you wish you knew before? Are you happy with your decision?

Everything is solvable. No one problem will define your company because there are so many to deal with at any point in time. Staying positive and understanding that everything has a solution is critical. Prioritizing and balancing the things that will have the most profound and meaningful impact on the business today and in the future will help you build a sustainable and successful business. Lastly, put in the work to leverage the community – while building a company is a monumental task, there are people out there that are willing and eager to help.

6. Any other advice you can share for others contemplating a similar path?

Believe in yourself and block out the noise. Managing rejection, hardships, and crises come with the territory when you’re a founder. Having an unwavering belief in your ability to manage the journey is critical to building a successful company and culture.

1. What were you doing before you quit your job?

Before leaving to start Kaskada, I worked as an engineer at Google and led a global open-source project under the auspices of The Apache Software Foundation.

2. When did you realize you wanted to quit your job?

I enjoyed the work I was doing, but eventually I felt that internal push to start building a team and a product I knew customers needed and that I was deeply passionate about. That said, if you had asked me 10 years ago where I’d be now, I never would have thought this would be my reality, but every day I’m thankful it is.

3. What initial hesitations did you have about quitting your job and how did you overcome them?

I had some early hesitations, but I’ve never shied away from making bold decisions. When I immigrated to the US from Croatia in my twenties, I knew I’d be a small fish in a big pond and need to work my way up. The decision to create Kaskada was the same – I was building on the work I had already done but I was still starting at the bottom.

4. Can you remember the day you put in your notice?  What was it like, what was going through your mind, how did your manager take it?

I was excited – executing on a plan after making a decision, that’s the easy part. It’s the first year that’s hard; building an effective leadership team, pursuing funding, all the early successes that are critical as the company grows. Success is never accidental, it’s a personal combination of putting in the time, networking, and iterating on your idea and pitch repeatedly. You must learn from the “no’s” in order to start turning them into “yeses.”

5. What are you doing now?

Most of my days are built around supporting my team and the company’s needs and engaging with others so I can continue learning and growing Kaskada. Before the pandemic, I was always out meeting with people face to face, and now that’s being somewhat replicated on video calls. I really value the opportunity of in-person exchanges both personally and in business, but for now video is a close second.

6. Looking back on your experience of founding a company, what do you know that you wish you knew before? Are you happy with your decision?

Every single day I love my job, and most days it loves me back. I’ve learned a lot about myself, people, and the industry by going through this and I have no regrets. At the end of the day, I want to live life to the fullest; just sitting around isn’t my idea of a life well lived.

7. Any other advice you can share for others contemplating a similar path?

Time is the most limited resource we have – don’t waste it living someone else’s life or working a job you aren’t thriving in. Seek satisfaction in addition to compensation.

1. What were you doing before you quit your job?

Prior to quitting my job to work on Nodesmith, I was working at Tableau in Seattle on Tableau’s Developer Platform. I worked for a few years as a Product Manager, and also for a few years as an Engineer – but the whole time I was focused on building tooling and APIs for external developers.

2. When did you realize you wanted to quit your job?

I had known for my entire professional career that I was going to do a startup, it was more a question of timing. I am fortunate to be in a field where I have the privilege to try a startup and recover if it fails – that’s an incredible privilege that not everyone has, so I want to make sure to acknowledge that. Pursuing a startup had always been a dream of mine, so I knew I was going to quit my job prior to taking it 5 years earlier, I just didn’t know when that would be.

3. What initial hesitations did you have about quitting your job and how did you overcome them?

 I think my biggest hesitation revolved around the fact that I loved what I was currently doing at the time. I loved the team I worked with, the technology we were building, and the company I was at. It was scary to leave that behind for the unknown. What helped me overcome that was leaning into the knowledge that we grow most in uncomfortable situations, and I craved that growth.

4. Can you remember the day you put in your notice?  What was it like, what was going through your mind, how did your manager take it?

It was tough! It’s always hard to move on from something; I definitely felt like I was letting my team down in some capacity. But my manager was very supportive, and that made all the difference to me. While he was sad to see me leave, we worked through a good transition plan that wouldn’t leave the team in a bad spot, and he clearly prioritized me as a person rather than me as a resource. Tech companies that I really respect are ones that foster a culture where it’s not seen as a bad thing for an employee to leave to start their own company. Treating that as a positive can lead to that employee one day returning or perhaps even bringing their company back via an acquisition.

5. What are you doing now?

I worked on my startup (Nodesmith, a blockchain infrastructure as a service company) for about 2 years. We built a great product that I am proud of, raised some money, went through Techstars Seattle, and learned a lot along the way. But ultimately, we didn’t reach enough success or see enough traction to continue to raise larger amounts of capital and grow. We decided to sell the product and our IP to another company in the space and move on. That was an incredibly tough decision, but I believe it was the right decision and I’m quite happy with where I ended up. 

About a year ago, I joined a startup called Shelf Engine as the second engineer. While I remain a huge fan of decentralized technology, I believe Climate Change is a problem that we need drastically more people working on – so I felt compelled to work on what I view as a more pressing problem. At ShelfEngine, we’re working on reducing food waste through automation. I’m very thankful to remain a part of the Seattle Startup ecosystem.

6. Looking back on your experience of founding a company, what do you know that you wish you knew before? Are you happy with your decision?

There are lots of things I wish I had known when I first started Nodesmith, as there were countless mistakes I made along the way. Naturally, we did not see the amount of success I had hoped we would, and there were definitely things we could’ve done differently with hindsight. That being said, I am so thankful I made the decision to pursue a startup. I have never learned more during any period of my life, and I met some truly fantastic people along the way.

7. Any other advice you can share for others contemplating a similar path?

The main piece of advice I have is probably the most clichéd piece of startup advice out there – and that’s to talk to customers constantly and ensure you’re solving something that’s incredibly painful for them. Anyone in the startup world has heard that countless times, I probably would’ve rolled my eyes at that “advice” years ago. But that’s really the only thing that matters, and it’s not an easy feat. That didn’t become real for me until the last few years of living it and failing to build something that would be indispensable to customers.

That, and make sure you begin this journey with a co-founder who you can count on and spend tons of time with. I was quite fortunate to share this journey with an incredible co-founder, and that made all the difference in how positively I view the past few years.

1. What were you doing before you quit your job?

Prior to starting VoiceHero, I had recently graduated from my Undergraduate studies in Business. I was fortunate to join a startup program called Next 36 which accepts individuals across Canada who are looking to start companies. There, I met my Co-Founder and we pursued this journey of building something new to add value to customers. I had worked several internships across various fields in marketing, accounting, non-profit, but wanted to give this a shot due to the opportunity, and given I’d be working with a network of highly ambitious and intelligent people to start “something”.

2. What initial hesitations did you have about quitting your job and how did you overcome them?

Although I didn’t necessarily quit my job after graduating from school, I had all of the thoughts about whether I should pursue a corporate job or start a company. Next 36 and the platform seemed to land on my plate and given some of my entrepreneurial experiences that I had in my undergraduate years, I thought it would be a good opportunity to start a company. I knew regardless of the result, I would be well-off and was confident the outcome would still take me far in my career.

3. What is VoiceHero?

My company, VoiceHero, is an analytics platform to help developers understand conversational user behavior on voice applications on services like Amazon Alexa and Google Assistant. The inspiration came when I was playing around with an Alexa and realized there were apps called Skills which highly resembled Mobile Apps. There were opportunities for customers to make purchases and enjoy delightful experiences. I decided to pursue this opportunity and ultimately joined the Alexa Accelerator Powered by Techstars.

4. What are you doing now? How did you decide to take a corporate job after closing your startup? Will you consider launching another company in the future?

Ultimately, our team decided to sunset VoiceHero based on various challenges including personal reasons, funding, growth and many more. In April, I started a role at Amazon as a Program Manager in the Partnerships and Roadmap Planning function for internal teams at Amazon to deliver features to the Alexa Mobile App. The idea of starting a company in the future would be great and I would highly consider it at some point again. But for now, I have the flexibility to think about what really motivates me and gets me excited now that all of the pressure of starting a company is out of my mind. I can work at my own pace and do it when I am ready. I’m not great at predicting the future, but it’s likely I will start another venture.

5. Looking back on your experience of founding a company, what do you know now that you wish you knew before? Are you happy with your decision?

Knowing what I know now about starting a company, there is way more thought that goes into starting a company. I had a great opportunity (moving to Seattle and meeting mentors like Sean J), platforms (Next 36, Techstars), and investors who supported me and my approach to entrepreneurship. But looking back, I honestly did not have a clear vision and plan at any given time. I had a drive for starting “something” and knew that’s what I wanted to do, but it was way too broad and required more self-reflection which never allowed me settle on anything. I started with everything else except for the problem and that problem pivoted drastically at times causing friction within the founding team. I am very happy with the decision to move on but I know the bigger decision to start a company requires much more careful long-term planning, vision, and co-founders to “start something”.

6. Any other advice you can share for others contemplating a similar path?

Find a problem or space you care about so much you lose sleep over it and that you believe YOU are the right person to solve it. It’s hard to have that level of passion and conviction but don’t waste your time until you think you have this. Starting a company is not this “cool” thing people just do for fun, it is very difficult in every aspect (mentally, emotionally, physically). Honestly, I haven’t found it yet and most people might never feel this way about a problem.

7. How did you manage wellness and mental health during your startup? You worked your ass off during the program, how did you stay sane?

I honestly didn’t stay sane. I was hyper-focused and tried almost too hard to solve every problem and let it get the best of me. This affected the people I worked with, especially my co-founder. All of that built up intensity, and sleep deprivation adds up and when things go south, it can completely deflate the team if you don’t have the mentality to bounce back.

8. Knowing what you know now, how would you go about finding a co-founder or validating an idea?

Work with someone long enough to tell that they are the person you want to pursue this long term with – think of it like a marriage (and I believe this analogy is accurate regardless of what people think). It takes years to build trust, and you need to accept and understand each other: from how you work together, how to motivate each other, lifting each others spirits when times get tough, and more.

1. What were you doing before you quit your job?

My previous experience was Amazon, Uber and most recently Convoy. I joined Convoy when it was roughly 30 employees, and was fortunate enough to see it grow to 1000+ over 3.5 years. When I left, I was leading the Operations org, and had an amazing team that included Operations, Customer Support, Program Management, Data Science, L&D and other functions.

2. When did you realize you wanted to quit your job?

A few people in my network had begun their own ventures – after talking with them about their experience, I started to consider entrepreneurship more deeply. I ultimately came to the decision after discussion with my family, but it was more about moving towards founding my own company then it was about quitting my job. I was afforded an incredible opportunity at Convoy, but didn’t have the time personally or professionally to “moonlight” – so founding a company meant leaving my role.

3. What initial hesitations did you have about quitting your job and how did you overcome them?

After coming to the conclusion that my wife and I would be able to support our family, the biggest challenge for me was moving on from the team I had established and cared deeply about. I came to the realization that I was mentally and emotionally committed to founding my own company, and it would be challenging to truly act in the best & long term interest of the team I had – so my departure actually made sense for both sides.

4. Can you remember the day you put in your notice?  What was it like, what was going through your mind, how did your manager take it?

I was fortunate to only have two managers throughout my 3.5 years at Convoy – both of whom I respected greatly. There were a lot of questions/thoughts running through my mind – was I making the right decision, had I truly considered what I was walking away from? I remained committed to the plan, and while the news was a surprise, it was also met with a great deal of support since they had taken on similar risks in their career.

5. What are you doing now?

Candidate was formally founded in January, and I’ve been full steam ahead doing everything – building the team, product, and service. After successfully raising a pre-seed, I was able to hire a team that I am thrilled to be working with every day. Even when times have been challenging (especially in 2020), having an incredible group of people who I get to partner with has made me truly excited to start work every day.

6. Looking back on your experience of founding a company, what do you know that you wish you knew before? Are you happy with your decision?

I had to learn the hard way that getting told “no” often is part of this job. Whether it’s come from potential investors, prospective customers, or others, it was different to receive than rejection I had faced in the past. These “nos” were either about me as a founder or my company, and at first it felt more personal. I was able to overcome this through 1) learning through each experience, 2) leaning on other founders who I developed relationships with throughout the journey and 3) using it as motivation to achieve success. I couldn’t be happier with my decision to found a company.

7. Any other advice you can share for others contemplating a similar path?

While it may be hard to swallow the risk that comes with leaving a safe role to start your own venture, nothing will match the daily joy you can find as an entrepreneur (in my experience). These two elements – risk and unmatched satisfaction – almost always come hand in hand, though.

Once you’ve started, focus deeply on your customers, users, and their experience. While the stories of rocketship growth are what we all dream of – and where the headlines are – it almost never happens without having a group of customers who absolutely love your service/experience/product.

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1. What were you doing before you quit your job?

I was a Senior VP at Bank of America, leading various information security risk related projects. It was a fantastic experience to work through multiple acquisitions of large financial institutions and related challenges.

2. When did you realize you wanted to quit your job?

As an immigrant family in the US, I’ve watched my parents start numerous blue-collar small businesses. Unfortunately, the businesses never resulted in financial stability, which resulted in my risk-averse mentality. As time went on and my career progressed in the traditional path, the stronger my entrepreneurial itch became. Giving up a great career may have appeared to be reckless to some family and friends, but my desire to build something of my own was too great to ignore.

3. What initial hesitations did you have about quitting your job and how did you overcome them?

My family (wife, 2 year-old daughter, a newborn son) and a mortgage were at the forefront of my mind. Being risk-averse, it took many years to make the jump while reading the popular startup books/blogs and searching for the right timing and opportunity. Eventually, I realized that there was never going to be the right time to make the jump. I overcame the fears by writing down the “worst-case scenario” on paper. When I saw that the “worst-case” was getting another white-collar job in a year, I couldn’t risk not taking a leap at least once in my life. I imagined what stories I wanted to tell my kids when they become older. My wife’s wise counsel and sounding board to balance opportunities and risks were valuable. It’s essential to prepare and bring your family along for the entrepreneurship journey (aka “no paycheck for a while”).

4. Can you remember the day you put in your notice?  What was it like, what was going through your mind, how did your manager take it?

To be honest, that day is a blur. I was really nervous, but after I put in my notice, I never looked back. I just made sure to leave on good terms just in case I needed to go back and ask for my job back. Here is the journey entry from that week:

I quit my job this week. Glad to be trying something different.  Friday is the last day.

Tomorrow is Thanksgiving.

[My son] is starting daycare full time next week.

Mother in law is leaving this Saturday.

Weblife [product] demo is on Monday.

I will have no paycheck starting next week.

I.AM.AN.ENTREPRENEUR.

5. What are you doing now?

I work for the company (Proofpoint) that acquired the startup that I co-founded (Weblife) with two other co-founders. We had a successful exit after three years.

6. Looking back on your experience of founding a company, what do you know that you wish you knew before? Are you happy with your decision?

I knew going into it that I was starting from zero, and needed to have a beginner’s mindset. I expected 100% on the job training. Throughout the startup journey, there were challenging times where everything was pressure tested (e.g., running out of money, stagnant growth). I was lucky to have a team of co-founders that trusted and relied on each other. Eventually, we made it through alive! I am thrilled with the decision to make the startup journey.

7. Any other advice you can share for others contemplating a similar path?

Make sure to have the foundations covered before making the jump (I recommend in the following prioritized order):

• family support
• co-founders you trust
• problem you want to solve

Also, have a beginner’s mindset and learn as much as you can during the journey. The experience we gain and the network we grow during the journey will be more valuable than the startup’s outcome. We can always do another startup! 🙂

 1. What were you doing before you quit your job?

I worked as a Software Development Engineer II on the Amazon FireTV team. I joined Amazon after graduating from college and worked there for 4 years. I worked on the Alexa Media Player that plays music on most Alexa-enabled devices, including FireTV.

In parallel with working at Amazon, I spent my 4th year pursuing a Computer Science master’s degree at Cornell University. It was a busy year!

2. When did you realize you wanted to quit your job?

I’ll prefix this with the fact that I always wanted to start a company one day. I knew that it wasn’t a question of “if” but “when”. While working at Amazon, I wanted to learn everything I could so that one day I could start a business. I decided to try as many “Amazon experiences” as I could handle. I owned several projects within FireTV and Alexa over the years, helped to release several devices and later I even helped to facilitate a PR demo of a new FireTV device. During my second year, I won an Amazon ideas competition, and had an opportunity to present the proposed product to over 40 different audiences. Now, I consider this “pitch practice”, but back then I didn’t know I was “pitching” a product – I was mostly interested in their feedback. After all of these experiences, I felt well-equipped to start my own business.

The time for starting Spiral aligned very well for both me and my co-founder, Andrew DiLosa. I had just finished a few projects at Amazon and graduated from Cornell. The summer after my graduation was the perfect time to start a company, and that’s exactly what Andrew and I did.

3. What initial hesitations did you have about quitting your job and how did you overcome them?

I’ve dreamed of starting a company for so long that in order to stop me the hesitations would need to be quite substantial. My parents were very supportive – they knew I wanted to found a startup for a long time. They also knew I would regret not doing it more than the possibility of losing some money or not enjoying the startup rollercoaster journey.

One hesitation I had was the financial aspect of founding a company from scratch. I knew I would have to live without a paycheck for a few months or years. During my time at Amazon, I purposefully saved money that I could spend on my future company. Once I had gathered enough finances to cover a few years of living expenses, I knew it was time to go for it.

Another hesitation I had was around leaving my Amazon team (Alexa on FireTV) – I loved working there. I kept learning something new everyday and I was enjoying my time on FireTV. In the end, I realized that I would forever regret missing this opportunity if I did not take it, and that it was the right time for me to start something new.

4. Can you remember the day you put in your notice?  What was it like, what was going through your mind, how did your manager take it?

My manager and I have gotten to know each other very well over the years and become very good friends. My manager supported my Amazon endeavors over the years like nobody else. He listened to my ideas, helped me to propose them, and supported me throughout multiple journeys as I tried to implement various projects within the company.

On the day I put in my notice, I flew into Seattle after my last day at Cornell and went into a 1:1 with my manager. He proposed a new growth opportunity to me, as he often did, and I told him that I really wanted to start a company and that now seemed like the right time for it. I think he completely understood why I wanted to become a founder based on the number of projects and ideas I proposed while at Amazon. He looked both happy and sad, and that’s exactly what he said – he was trying to keep me on the team, but at the same time, he was also very happy for me for starting a company, which I’d dreamed of for a long time. He knew me very well, so he understood that there was no way to keep me once I’d decided to change paths. I’m still very good friends with my manager, and I really hope we get to work together again one day!

5. What are you doing now?

I’m the co-founder and CEO of Spiral, a Seattle-based AI company that scans customer feedback and detects emerging issues before they escalate. I meet with customers, fundraise, lead product development, do business development, conduct hiring, and anything else we might need at Spiral.

6. Looking back on your experience of founding a company, what do you know that you wish you knew before? Are you happy with your decision?

I wish I knew more about customer discovery. As typical engineers, we started our startup journey with building a cool app. We created an AR app for teleporting others into the same room. Eventually, we learned that a cool app doesn’t necessarily make for a good business. We pivoted completely and worked backwards from the customer to define our new product. Here is how we learned customer discovery:

While working at Amazon, we were getting a lot of customer feedback in various forms and couldn’t always tell which bugs were more important than others. We became curious if other companies also collect customer feedback and apply it. After conducting over 70 customer interviews, we found that most companies collect tons of customer support conversations, but it’s often hard for them to find key customer issues. As a result, we started to take in companies’ customer support data like emails and chats, and detect emerging problems before they blow up.

And yes, I’m very happy with my decision – I’m glad I took the leap and founded Spiral! These were the two craziest, quickest, and the most challenging years of my life! Even if my startup journey would have ended for me today, I would say that the learning experience alone was totally worth it. I’m not sure I can think of any other way to gain this experience.

7. Any other advice you can share for others contemplating a similar path?

Here are a few pieces of advice that would have been helpful to know from the start:

Just go for it. When contemplating founding a company while working elsewhere, don’t worry about the current state of the idea and the product you have developed so far. It takes months or years to get to the right idea. Most founders I know iterated or pivoted a few times in the process so it almost doesn’t matter what you start with. It takes time to find the right problem and solution to base your company on and, in fact, that’s the goal of the first two years of your journey. All of this is hard enough to do without a full-time job and even harder when you have one, so my advice is if you’ve been wanting to start a company for a long time, have a plan in mind and enough resources available – just go for it.

Don’t be afraid to pivot. It’s very rare for a startup to be successful with the initial problem and solution they started with. Most founder stories I have heard always include a twist and a pivot in one way or another. If you’ve exhausted all the options for tackling your current problem and your customer discovery is in the “meh” state, think about other problems that came to mind over the past few months. A pivot symbolizes an ability to iterate, responding to a market change, or taking a new customer behavior into account, so it’s no surprise that many successful businesses have pivoted in the past.

Don’t write code (it’s a challenge!) before you hit at least 50 customer interviews. Customer discovery is everything. The most common mistake I see is implementing a product without any input from your future customers. We’ve made this mistake at Spiral – luckily, we learned customer discovery at Techstars, so we were able to get back on the right track pretty quickly. Also, customer discovery never ends – it’s a continuous loop of asking customers about their problems and verifying if your current solution is solving the same problem.

1. What were you doing before you quit your job?

I spent two amazing years as the Director for Product/Design at TINYpulse, a Seattle-based employee engagement company. Prior to that I spent 10 years at Microsoft after graduating from the University of Washington in 2006.

Throughout my career journey I always felt like an entrepreneur/intrapreneur at heart and venturing out to make an impact in my own way was always a career goal of mine.

2. When did you realize you wanted to quit your job?

I guess you can say I gave TINYpulse 2.5 years notice versus 2 weeks :). Working at TINYpulse was a dream come true for me, and a huge part of that had to do with the support leadership gave me and the team. I remember interviewing with David Niu, TINYpulse’s CEO and he was really keen in the interview to learn about my goals and ambitions. I told him in the interview after making a big impact over the next several years at TINYpulse my dream is to start my own thing, and he supported me every step of the way. I always felt the best way to land and prepare for your next role/venture/adventure is to do a damn good job of your current one, and that’s what I attempted to do before leaving.

3. What initial hesitations did you have about quitting your job and how did you overcome them?

The biggest question in my mind was around how I could pursue my passion and still support my family, as my wife wasn’t working and was home with our two young kids (a much harder job than I had, I might add!). This was also part of my “why” behind wanting to start my own business. I wanted to create something my kids would be proud of and make an impact as a founder. Tactically speaking, figuring out things like insurance benefits and making sure I’d have enough of a base salary to live off of were huge. I know I wanted to make the jump so really the logistics were the only barrier (that said barriers like that can often pile up and prevent people from making the jump). Our startup’s runway wasn’t just about the startup’s survival, but my entire family had a “runway” in many ways which was attached to the company’s success and that could be overwhelming to think about. My co-founder Andrew was in a similar boat and that really helped! I overcame much of this through networking with others who had followed this same path – and I soon learned many perceived barriers were not as daunting as I assumed.

4. Can you remember the day you put in your notice?  What was it like, what was going through your mind, how did your manager take it?

It was tough. I loved the team at TINYpulse. I also wanted to do things the right way, and was able to work out an arrangement with our leadership team that let me ensure the transition happened in a gradual and effective way.

The day I communicated my decision was tough – I wanted our CEO and my manager to be the first to know and telling them was not easy. We had lots of exciting things happening at the company (as with most scenarios like this there is never a perfect time to leave) and I didn’t want my manager and team to be disappointed and feel I was abandoning them in any way.

People leave jobs for many reasons, and while not always possible I find it best to run toward things, not run away from things. I was making this decision because I was running towards a new opportunity. Thinking that way made the conversations easier and I was surprised at how supportive everyone was.

5. What are you doing now?

Living the dream! It’s been an amazing year+ growing our business, Humanly.io, and bringing equity and efficiency to high volume hiring processes. It’s been a blast growing the team, adding new customers and delivering on our mission in automating candidate screening, scheduling and engagement at scale. One of the biggest parts of our success has been centered around bringing others along on the journey with us so it’s been great to have folks at TINYpulse, Microsoft and other companies we’ve worked with cheer us on!

6. Looking back on your experience of founding a company, what do you know that you wish you knew before? Are you happy with your decision?

The importance of surrounding yourself with audaciously ambitious voices. You need to be practical as a founder, but not TOO practical. Having people around you that do more than give advice but push you through their irrational audacity is big. You can never think big enough, and sometimes it’s too easy to think your “big” thinking is big enough.

7. Any other advice you can share for others contemplating a similar path?

My main advice I’d give, and one I live with when making any life decision is to never start the decision making process by asking yourself “would I regret doing this?”, but instead start by asking “would I regret not doing this”. When you think in those terms often you could make the argument that you are risking your life (happiness, future…) by staying put in your current situation.

1. What were you doing before you quit your job?

I was a philanthropic consultant and marketing manager at a non-profit in Perth, Western Australia.

2. When did you realize you wanted to quit your job?

I had achieved a lot of success and been provided a lot of opportunities by a very supportive board and CEO, but the only next step was to either take over my CEO’s position or move to another similar role in another company. I knew I needed a new challenge, and felt unsatisfied by the opportunities that existed for me at the time. I always knew I wanted to run my own business – but wasn’t quite sure where to begin. I started out helping others with their companies (and started 5 companies in 4 years!). I was in the process of getting ready to take over one of the companies as the original founder wanted to leave, and a mentor gave me some great advice: “If you can look me in the eye and tell me that this (running this company) is what you want to do everyday for the next 10 years, I’ll help you with everything I’ve got. But if you can’t tell me that, I don’t want you to say yes to this role”. I knew and I knew in that moment that I didn’t want to run that company, but that I wanted to pursue running my own company and focus on creating experiences and events that left a lasting impression on hosts and guests alike. That was my “aha” moment.

3. What initial hesitations did you have about quitting your job and how did you overcome them?

I was so worried I’d fail! I still am sometimes! I received some great support and advice from mentors and friends, but the best way I found to overcome the fear of failure was to play what my partner and I call the “worst case scenario game”. We think through the worst case scenario of a particular situation, and if we can still handle it, then we know we will be ok. In taking the leap to start Voyager’s Table (www.voyagerstable.com), I thought through my worst case scenario which was returning home to Australia, tail between my legs, having spent all my savings and using up all the money I’d invested. My worst case scenario is/was going home, living at my parents place (at 40?), and crying myself to sleep on their couch until I could get myself back up and go out and get a job waiting tables or making coffees til I got my confidence back up to try something again (minimum wage in Australia is $19/hr, so you know, really, pretty good considering the free rent on mum and dad’s couch…haha). Since that was my worst case (thankful for all my privileges here!), I figured I’d better give it my very best shot.

4. What are you doing now?

Voyager’s Table has been running for almost 4 years now. What a crazy fast journey it has been. We have a team of 5 full time and a crew of regular part-time and contractor events, talent and media team members that are SO amazing and we’re so lucky to have them as part of our journey.

A bit about Voyager’s Table:

We’re an event production, media and talent hospitality company that specializes in designing experiences for powerful connection. Whether we’re hosting world leaders or helping companies keep teams connected in person and online, we take personal ownership of every event we touch. Pre-pandemic we: produce festivals and experiences for 60,000 ppl –> 6 person private dinners and everything in between and have a niche expertise in talent logistics and hospitality (eg. accommodation, scheduling and hospitality for 120+ celebrities and world leaders in South Africa for event headlined by Beyoncé in 2018). During the “Great Disruption of 2020”, we’ve been busy producing high-impact/engaging online experiences for teams and communities across North America, and curating local market kits & recipes to support our vendors impacted by downturn.

On the 12th of September, we’ll be hosting our annual night market, this year all online, with an incredible line up of creatives sharing their talents with you, with activity kits available for delivery/pickup in Vancouver, Seattle and New York so you can join in the fun from home. Details and lineup here: voyagerstable.com/nightmarket

5. Looking back on your experience of founding a company, what do you know now that you wish you knew before?  Are you happy with your decision?

I wish I’d done this earlier! But also, I’m glad I have had the path that I did – I learnt so much helping others with their dream businesses, and shouldering lots of responsibility as an interim or start up CEO. I’m so grateful for those opportunities and for mentors and past employers who saw my potential and encouraged it.

6. Any other advice you can share for others contemplating a similar path?

Surround yourself with solution focused and supportive people (one of the reasons I love the Venture Out community!). And most of all: if you know and you KNOW in your heart that this project or business is what you REALLY want to put your heart and soul into for the next 10 years – DO IT and DON’T QUIT. Get back up and keep going – hone your craft, grow, get better and smarter and wiser and learn, learn, learn. But don’t stop trying and don’t wait for someone else to give you permission. Good luck!!!