via Geekwire and Taylor Soper

“It’s a great time to start a company.

That’s the mantra at Venture Out, a Seattle-based 12-week program that aims to help tech workers leave big companies and create their own startups.

The organization launched last year and is now accepting applications for its second cohort that kicks off July 13. It also recently raised a $700,000 investment round led by Microsoft’s VC arm M12. Other venture capital firms including Founders’ Co-op, Flying Fish VC, and Liquid 2 Ventures invested.”

About a year ago, I had a tough conversation with my manager. I hadn’t been happy about some changes to my role, and it was showing up in my work. I realized I had a choice to make: stay there and really commit to my job as it was or let go and do something new. Being half-in/half-out wasn’t working. I agonized over the decision. There’s more than a little truth to the phrase “Amazon is where overachievers go to feel bad about themselves.” I had gotten so much out of my time at the company, grown so much, accomplished things I was truly proud of. Did I really want to leave on a sour note?

One of the odd things about working in HR is that anytime I was struggling personally with some issue at work, someone would walk into my office and want to talk about what they were struggling with and it would turn out to be the same thing. I would listen and nod sagely while they laid out their problem. I would ask them questions about what they had tried and what outcome they wanted. I would give them advice and talk to them about next steps. And after they left, I would think, “Dammit. I guess if I’m going to give them that advice, I have to take it.” People don’t like taking advice. Here’s why: if you need advice, usually your next steps are hard and scary and messy.

I decided that my lack of engagement in my role meant that it was time for me to move on. It simply wasn’t where I wanted to be anymore. I had learned what I needed to learn and staying there to prove something wasn’t actually a good reason. But what was next? I loved being an HR Business Partner. It’s a tough job. You wear so many hats, get to take a true leadership role, and get to make a difference on an individual and structural level. Did I want to continue that at a different company? Or was it time for a bigger change?

I want to take a moment to talk about why I’m telling the story this way. It’s vulnerable and uncomfortable for me. I worry that shining a light on the rough parts might cost me investors and customers. I could, without ever lying, just tell the good parts of this story. The parts that make me and my company sound like a great investment. But there are big reasons I’m doing it this way. One is that integrity is a core value for myself and my company, true integrity, not lip service. Another is that I’m sure there are other founders or people considering being a founder that are wondering “if my corporate job isn’t going so hot right now, do I really think I’ll do better if I try something harder?” I want those folks to know they are not alone. And finally, being open about what I was struggling with is how I found my business partner and my problem to solve.

On a cross-country trip to visit friends, I talked about what I was struggling with at work and the choices I was debating. I asked my friend, Julian, “Hey that thing you’ve been working on nights and weekends, do you maybe want a partner?” Their enthusiastic “Yes!” was both exciting and scary. I could really do this. On the plane back to Seattle, I got a text from another friend I’d been open with. He talked about a problem that needed to be solved and that he thought I could help solve it. It was ambitious – do it right and take a chunk out of climate change, but not too ambitious – yes, I did think we had the skills and knowledge base to do it.

When I got back, I had a very honest conversation with my boss. I shared that I was ready to move on and we talked about the best ways to handle the transition. I felt lighter. In the time since, I have found that I am more engaged, more productive, and back on a learning curve that sometimes feels vertical.

Here’s what I learned from the experience:

1. You have to be willing to ruthlessly prioritize. In life, and in a startup, you will never be able to do everything perfectly. Choose what’s most important to you and go after it. That will mean letting go of some things you thought were vital to you. Don’t chase someone else’s dreams, even if that person is a past version of yourself.
2. Get yourself into an environment that makes it easy to be in a growth mindset. If you are in a place where blame is heavy and mistakes are seen as something other than a learning opportunity, start building your plan to get out. You will never become your best self if you have to pretend you already are there.
3. Build a team that values your strengths and supports your needs. Nothing is inherently easy or hard. Things are easy or hard for you, right now. Who makes hard things easier for you? Who helps you tear down barriers? Especially for gender and racial minority founders: your strengths have been systemically undervalued your whole life. A team that values you will help you undo the damage that comes with that. For founders who are in the majority: what have you been taught to undervalue? Make sure you don’t ignore that when you build your team.
4. Be brave. I believe bravery is about choosing the right path, independent of how scary that is, recognizing the fear that comes along with that, and doing what you need to do to move forward anyways. What does your still, small, inner voice tell you? Follow it. Your team should have your back.
5. Be vulnerable. That is the most effective way to find what you need.
6. Change the world. The world is broken, y’all. If you didn’t know that before COVID-19 hit, you know that now. As a founder, you are saying that you believe something needs to change. There is a problem that needs to be solved. You are declaring yourself the person to solve it. Own that. Think about how to build it into the values of your company. Look for lots of advice, but only take the advice that fits with your vision of the world you want to build.
7. “If a thing is worth doing, it is worth doing badly.” – G.K. Chesterton. The data say that you will most likely fail if you found a startup. Fortunately, there is a lot to be gained through failure. You can choose to do something easier than start a company. If you start one anyways, get comfortable with the idea that you will have to do a lot of things badly before you can learn enough to start doing them well.
8. Look for the advice that helps you not make the mistakes you are naturally inclined to make. If you are the kind of person who jumps off a cliff whenever you get the chance, you don’t need me to say “Do it!” The people who need that advice are the people who are going to stay in a situation that is harming them because change is hard. What advice is hard, but necessary? What advice do you think you need to walk away from?
9. Don’t build a company by and for only white men. Seriously. Don’t try to fix your diversity problem a couple years from now. You won’t be able to and you will have only yourself to blame for not starting from the beginning. Don’t blame the pipeline. Don’t blame schools. This is something you own. Start thinking about it day one.

Now that I’ve written out all that advice, I guess that means I’m committed to taking it. Since my partner and I have both left our jobs to focus fully on our company, I believe we’ve made a good start. I still have no idea if we will be successful, but I believe we will be. We will find out.

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We are thrilled to announce that Venture Out has received support from M12 – Microsoft’s venture capital fund – and an incredible group of 30+ early stage investors, including Flying Fish VC, Founders’ Co-op, Liquid2 Ventures. This support signals that employees should be encouraged to moonlight, a term used to build a startup while working in your day job.

With the support of these investors, we are opening applications for our second Launch program on May 18th. We have enhanced the program to provide more curation for each founder and due to demand, we will start a new Launch program every two months with rolling applications.

Venture Out started in 2018, when we brought together a handful of Seattle startup founders with the simple goal of supporting one another on our startup journeys. All of us had three things in common: We wanted to build something great, we had experience working at Seattle’s big tech companies, and we were nervous to leave the security of our day jobs without a strong support network.

What started out as 20 builders and technologists has grown into more than 200 founders building some of the world’s next big technology companies. Once a month this group has come together for direct founder to founder support. VO members crowdsource answers from other founders who have been in their shoes – finding answers faster and avoiding common pitfalls that trip founders up. The foundation of this community is a shared value of giving back and giving first.

We’ve since doubled these events to twice a month and taken them virtual – but the ethos stays the same. Founders supporting other founders courageous enough to venture out of their day jobs and build something new and valuable to the world.

Eighteen months into this journey this community of founders sought more support from Venture Out, so, last December we launched our first Venture Out Launch Program. We surrounded eight startups with successful entrepreneurs, investors and mentors in order to help those founders validate, launch and accelerate their startups.

We are excited to continue supporting founders in the Seattle ecosystem and beyond.

Learn more about Venture Out

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

Leading global Product and Design teams at Axon (www.axon.com), a $4B tech company. Oversaw five major product efforts – two in hardware and three in software; as well as setting the global vision for a consolidated product suite that offered unique and significant value to our end users.

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

When I found myself spending more time in admin and corporate meetings, putting together decks and reviewing spreadsheets, than I was on users and customers, developing new and valuable product ideas, and shepherding them through the development process. It is exceedingly rare for senior company executives to be creators – their principal job is organizing the rest of the company to enable creators to do their very best work, and then hold those creators accountable for hitting a very high standard of performance. I found I’d rather have more creation and less executive planning sessions.

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

What stops most people, I’ve found, is not money or talent or even a good idea. It’s being completely unafraid to be publicly wrong. Most highly talented and intelligent people, no matter how humble they are, secretly believe they’re right far more often than they’re wrong, and arrange their lives so that the world they live in feeds an affirmation of this belief back to them. Quitting a full-time job to start something is leaving a world where you have been 90{7da1b4016315e6906389b7680f0f0ab0dbfee16dff356723890b92cef8bfc446} right and 10{7da1b4016315e6906389b7680f0f0ab0dbfee16dff356723890b92cef8bfc446} wrong to enter a world where you are at least 90{7da1b4016315e6906389b7680f0f0ab0dbfee16dff356723890b92cef8bfc446} wrong and only 10{7da1b4016315e6906389b7680f0f0ab0dbfee16dff356723890b92cef8bfc446} right.

I overcame this in two ways. First, I’ve done enough things in my life, like serving in the Marine Corps, that losing some money and having a bad business idea doesn’t really scare me. Second, and more usefully for others, I had a friend give me this framework: “A good startup takes something that is entirely broken and tries to unbreak it, a little bit at a time.” Everyone who’s naturally a builder likes to take broken things and make them work, and putting it in this broken/unbroken frame, rather than a failure/success frame, helped quiet those dastardly little negative voices in my mind telling me not to try.

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?

Yes. It felt like a release, and made me fundamentally happy. I’ve never spent a single minute second-guessing it.

5. What are you doing now?

Helping people get paid fairly. We do this by evaluating their offer letters and supporting them in the negotiating process as they change roles; and by providing market data to determine whether they’re currently being paid fairly if they’re already employed. We help people increase their compensation by tens of thousands of dollars, but the user feedback is the real gas in the tank. People are alone and anxious in this hugely critical moment in their careers, and we do our best to be there for them, and support them, as they make a transition.

6. 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?

Starting a company is about as close as you can get to a maximal professional learning experience, which is why everyone who does so writes a book about it (or at least tries to). Of everything I’ve learned so far, the two that stand out the most are:

1. Teams win. A good co-founder is better than a great business idea. Don’t go it alone if you can avoid it.
2. Emotional resilience is more important than intellectual strength. In startups, everything is broken – and remains broken, day after day after day. And you have no excuse, no external factor, to point to as an absolution for your failed effort. Build your ability to face public and repeated failures with equanimity and resolve.

I could not be happier with my decision. As with having kids and getting married, my only regret is not doing it earlier. Five stars, highly recommend.

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

Each startup success has the unique factors that made it so, and every startup failure has the same. The best extrapolation I can give you is to hone your business instinct for what might work and what might not in every aspect of a technology business. Only at big companies do you have the time and data to make comfortable decisions. Unfortunately, the speed at which those companies operate means you won’t get enough practice attempts at uncomfortable decision-making just by working there. So here’s some ideas that can accelerate your learning:

• Build a ten-slide pitch deck – on any idea – every week, and share it with a friend or colleague who’s not afraid to engage seriously with it and tear it apart in front of you.
• Do a UX teardown of a product you admire and build what you think their roadmap should be. Who are their user personas? What’s the value prop and business model? What are the buyer alternatives? What are the design choices being made? What feature should be dropped, and what missing feature should be added?
• Build a simple website, integrate payments, content, and social, put some ads up somewhere – find out for yourself what’s hard for you, and what’s not.
• Figure out your own ways to force yourself to get more practice in product and business ownership so that when you do make the big leap it doesn’t feel big at all.

And, lastly, don’t sweat the failure. That equity vesting package you’ve currently got is just a narcotic administered by your corporate overlords to silence the voice inside you saying it’s time to build the thing you really want to build. They’ll always be there if you ever need to go back. Go get building.

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