The Day I Ventured Out – David Krieger, Co-Founder & CEO at Stealth Res-Tech Startup

October 22, 2021

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

I spent the last 10 years at Expedia leading strategy, business development and product across several lines of business. Most recently, I led strategy for Expedia’s transportation businesses (air, car, cruise) while also forming a product innovation team tasked to build future mobility experiences and offerings.

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

I was attracted to entrepreneurship from an early age: fostered and cultivated watching my mother take the leap from big company to building and managing her own franchise business as a single parent. I admired her fortitude, creativity, and ability to define her own success, and I also envied the freedoms of running a business.

For years, I gravitated to roles where I could interact with and support founders, without fully committing. Early in my career, I was an investor and consultant with the World Bank/IFC/Grassroots Business Fund and had the great fortune of supporting and investing in early-stage companies across Africa, Asia and Central America that delivered double bottom line returns. Later in my career, I launched an incubator team at Expedia to facilitate partnerships with travel tech innovators. Surrounding myself with entrepreneurs gave me brilliant snapshots into that world – both the excitement and the challenges – and left me plotting future roles.

In 2018, while on paternity leave, I joined the Seattle Angel Conference as an investor. That was likely the turning point when I mentally committed to move into an operator role at something early stage. I spent the next few years exploring different opportunities and ideas, and in mid-2020 I landed on the idea that would eventually lead to my current role as co-founder.

Getting to the point of quitting to pursue the startup full time required hitting specific milestones that my co-founder and I agreed to early in the process. These included: volume of stakeholder interviews/research, commitments from customers to pilot, and interest from investors to contribute alongside our bootstrap dollars to fund the early path to product market fit.

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

The two biggest factors weighing on me were 1) an awareness that I still had more runway left in my Expedia career, and 2) the fear of failure.

My decade long tenure at Expedia was full of reward; great mentors and peers, fun and exciting industry, and roles that pushed me to learn and grow. Leaving this environment was always going to be tough. I felt doubt, fear, and guilt: would I be letting the Expedia team down, am I competent enough to start something from scratch, if my startup fails will I have derailed my career path…?

None of these are unreasonable concerns. To overcome them, I had to really believe in the idea that I was to pursue. Research and positive signal helped build the momentum and excitement needed to offset the anxiety of leaving my comfort zone.

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?

The day I gave notice was extremely stressful. My technical co-founder had already left his full-time job and was waiting for me to join him. I wanted to give my manager plenty of advance notice; leaving on good terms was extremely important. Despite having a great relationship with my manager, I anticipated a negative response ; my thoughts ranged from “will they walk me out?” to “will they push to change my mind?” …

When I finally met with my manager, he took the news with surprise, but encouragement. The thought that kept repeating in my mind was “no going back now!”
Apprehension was quickly replaced with excitement and relief. After nearly a year of moonlighting and worrying that I was inadvertently shortchanging everyone in my professional orbit (Expedia and my startup co-founder), it was exhilarating to be able to talk openly about this new opportunity and transition my attention to the next stage.

5. What are you doing now?

After taking a few weeks to ramp down at Expedia, I am now fully operating as co-founder / CEO of a stealth-mode res-tech startup aimed to improve and refine the homeowner and home management experience. We recently closed on a pre-seed raise, launched a beta prototype with an initial cohort of users, and are lining up several larger pilots for later this year.

I’m excited to share more soon.

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 have zero regrets with my decision, and at this stage am fairly satisfied with the methodical approach we took. My partner and I spent 3 to 4 months upfront researching our core hypothesis and business idea with stakeholders (and continue to research to this day), built a prototype and lined up investment and customer commitments before we took the leap to working on our business full time.

The moonlighting approach was not easy. Progress can feel slow and it’s hard to constantly context switch between two jobs. The stress creates plenty of inflection points where it feels easier to quit. And it is amplified by the fact that you’re not just juggling two jobs but also searching for time to prioritize the other important things in life: i.e., being an attentive husband and father, exercise… sleep… So, I suspected I would be pulled thin, but I don’t think I had realistic plans for what could be accomplished. Some things do fall by the wayside, and I do wish I was more proactive at planning which commitments would take a back seat.

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

A few quick pieces of advice:

  1. Build your support network and use it early and often. Everyone in your network has a purpose. Friends and family can provide emotional support but it’s also important to cultivate a network that can provide constructive, unbiased feedback and advice. Venture Out has created a fantastic community of founders, mentors, and investors in Seattle and it’s been a tremendous boost to have that knowing audience available for guidance when needed.

Educate yourself on some of the minutia, like accounting, tax and legal. I’m not saying to do everything yourself, but it is important to understand the key terms and issues, so you are prepared for conversations with investors and partners (and so that you don’t overspend on professional services!).

2. Really understand the problem you’re solving. Speak with as many potential stakeholders as possible; if you’re building a multi-sided marketplace, be sure to understand both the suppliers and the customers needed to build engagement. Before getting comfortable investing in a prototype build, we spoke with at least 50-100 potential customers and stakeholders to understand what motivates their behaviors. Even after building out the first iteration of our product, we continue to engage with stakeholders, letting their voices influence the direction we take to improve how we solve a problem.

3. Entrepreneurship is an investment. Leaving a corporate strategy job to start a company is the fastest path possible to test my ability to execute and operate a business. There’s no such thing as a free ride. This is a massive investment in my professional toolkit, and when I think about it in those terms, there is really no way I can lose.

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