Trade shows are an effective customer acquisition strategy, especially for startups. Now that businesses are going back to in-person events, this is an opportune time to plan for your upcoming trade show. Unfortunately, most startups don’t yet know the tips and tricks to generate a high ROI from their trade show. With just a little added effort, the ROI on your tradeshow will more than pay for itself.

Having seen it all from spending six figures at trade shows with Amazon, to spending only a few thousand dollars as a startup, here’s how to maximize the value of your event:

1. Location Matters. Purchase a double booth instead of a single booth, and opt for a corner booth, if available.
   • Being easily recognizeable at a trade show is important. A larger booth not only allows for more customers to engage with you, it makes it easier for them to find you.
   • Return on Investment: The numbers here are illustrative, given that your booth costs vary and the price of your software will differ, but let’s say a single booth is $3,000 and a double booth is $5,000. Compare this number to the price of your software. $30K ACV? Huge ROI after one new customer. $2.5K ACV? You break even with just a few customers.
2. Bring at least three employees to represent your company at the trade show. You should anticipate having two employees in conversations with customers while a third person is attracting attendees to check out your booth, handing out swag, restocking supplies, giving a break to others on your team, etc.
   • It is always good practice to have someone walk the tradeshow to visit other booths to learn about competitors and build connections. At a minimum you should have two people stationed at the booth and a third person to manage everything else.
     • Pro Tip: Meet your competitors. Get insights into their product. Listen to how they talk about their product with prospective customers. Play nice with everyone. You never know…someday you might acquire them or visa versa.
   • Ensure everyone is wearing your company’s logo, has a name tag, and are easy to distinguish from the crowd.
   • Arrive on location and inspect your booth at least twenty four hours in advance of the trade show starting. There is always a last minute thing you’ll need to setup your booth from an extra power strip, duct tape, etc.
3. Make your booth as inviting as possible
   • Order TV monitors from Amazon or pick them up at an electronics store before the event. Patrons are attracted to screens. Have two monitors hooked up to laptops running a loop of your product demonstrating its features and slick design.
   • Have a customized table cloth over your trade show table with your company’s colors and logo on it.
   • Get banner stands to make your booth pop.
   • Get banners made to go over the pipe and drape / back wall of your booth.
   • Pro Tip: Have two tablets or laptops nearby so prospective customers can test out your product in a demo instance AND purchase a subscription on the spot.
4. Provide swag to existing customers attending the trade show. This will make them walking advertisements for you. Your best referral sources will be from word of mouth, so give everyone something to talk about.
   • In advance of the tradeshow, identify existing customers that are attending the tradeshow and send them your company’s swag to wear or share with others. Tell them that for being such a valued customer, you are sending them swag for the tradeshow to wear, if they’d like.
   • Pro Tip: Offer existing customers a free month of service for anyone they refer to you who signs up for a subscription.
5. Good-quality swag goes a long way. You can’t be everywhere all the time, so let your swag speak for you.
   • By creating good-quality and functional swag that people want, they will use it at the tradeshow. This will help you create more awareness for your company. Pens with your logo on them (and not the cheap bic pens) work great. They go right into someone’s pocket and can be seen throughout the tradeshow as people take notes.
6. Bring a fishbowl for raffle prizes.
   • Driving traffic to your booth is paramount and having patrons return for a second (or third) time is even better as it increases their consideration to purchase your product. Create raffle prizes for people to win (and make sure the raffle prizes are something people will actually want). Prizes could a free annual subscription to
   • Ask patrons to drop their business card into the fishbowl (this is an easy way for you to get contact info from patrons) and announce the winners daily, or every so often depending on the length of your trade show.
7. Schedule in-person meetings at the trade show with existing customers. Your customer discovery process should never end, therefore, continue building relationships with your existing customers. Ask them about their unique insights with their business, what is working, and what isn’t. Become a trusted partner and build those relationships!
   • Pro tip: Make it a point to connect with the leadership team of the industry association putting on the trade show. This could lead to them spotlighting you in an upcoming article, future advertising opportunities, introductions to others, and more.
8. Create a sign-up sheet for in-person meetings with prospective clients. Spending 15-20 minutes with each prospect helps you build a relationship and makes it more likely to convert a prospect after they feel that you understand their business and can help them.
   • This also helps drive repeat prospects back to your booth. The more the merrier.
   • Pro tip: Have a quiet place near the trade show floor reserved to conduct these meetings.
9. Setup after-hours, invite-only, events at the conference.
   • This could be a happy hour or dinner event. Happy hours are usually equally effective and cheaper. Save the dinners for special clients or a team bonding event.
   • Comprise 50% of the attendees to this invite-only event with your existing customers and have the other 50% available to prospects you are hoping to close. Let your current customers do the work of explaining how great your software is to the other 50% so they do the selling for you in a very authentic manner.
   • Ask the trade show management for a list of attendees to the conference in advance of showing up. This does not always happen, but try to obtain who all will be there in advance to cherry pick which companies you would like to connect with. Also, let your existing customers know that you are attending the trade show and that they should stop by to visit you there.
10. Trade shows can be exhausting. Consider the following options to make things easier:
    • Stay at the hotel where the conference is being held instead of renting an AirBnB or hotel offsite to save on costs. Reducing the back and forth travel time to the conference center is worth it and some of the best meetings take place before or after the trade show starts, so make sure you are on site.
    • Make dinner reservations in advance for your team and/or any special customers. Everyone will be trying to make last minute reservations, so do this in advance and you’ll come out ahead.
    • Give your team members a day off the following week to recover from the trade show. Let them use this time to recover and follow-up with prospective customers.
11. (Bonus) Offer trade show-only pricing for anyone who purchases a subscription to your software on the spot.
    • Make the promotional pricing attractive. Depending on your company, this could entail:
      • First two months free when you sign up for an annual contract
      • Waiving the onboarding or data migration fee
    • Pro Tip: Come prepared to accept payment on the spot.

These tips should help you create a huge ROI for your trade show. Assume a 3-day conference, you will generally spend the following:

• Travel, lodging, and expenses for three employees for three nights might cost $4,500.
• Cost of booth, swag, marketing materials, business cards, etc., might cost $6,000.
• Hosting an invite-only happy hour event might cost $2,500.
• Total Estimated Costs: $13,000

Now consider how many new customers you acquire and the ACV of your software. With just a few new paying customers at the trade show, and many new prospects, your trade show should pay for itself in short time.

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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?” …

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.

“If you want to go fast, go alone. If you want to go far, go together.” – African Proverb

The value of a startup community is often an overlooked ingredient of accelerating startup success. Startup communities are a self-sustaining ecosystem connecting like-minded founders, mentors and leaders from all walks of life to solve the most pressing startup problems to successfully launch a startup.

These startup communities provide an integral support system for inspiration and knowledge that is vital at various stages of the startup’s growth. A wide number of startup communities target different industries, niches, or growth stages giving entrepreneurs options to find the ideal fit and benefits. Let’s take a look at the upside of joining and participating in a startup community.

Considering quitting your job to launch or join a startup? Learn more about our Big to Small Lab

Strengthen your founder/mentor/investor network to increase the chance of startup success

Startup communities bring together bright, creative, and innovative people ambitious to not only solve challenging problems, but to provide collaboration and support to others. By joining a community, entrepreneurs can change the traction and trajectory of their startup. 

Got a problem? Sometimes the solution may not lie within you but within your network. Being on the receiving end of years of knowledge from other experienced professionals is a key benefit of aligning yourself with a community of entrepreneurs. As trust begins to build, so does establishing a long-term mutually beneficial relationship which could transform into a valuable mentorship or partnership.

Need a partner or even a potential co-founder? Community and event gatherings open up incredible networking opportunities with other professionals to partner with which can further advance startup success. You may even find the perfect co-founder to complement your vision and skills within the community. With time, you’ll build confidence and trust to help each other out such as giving references and referrals. The professionals in the community not only want to help boost your startup but the community as a whole. 

Need an investment? Investors are an integral part of the startup community. They offer a unique lens into the experience of investing in other companies and can also provide valuable advice in the lens of what investors are looking for. They are actively interested in investing in great startups ready for the funding to help propel their growth.

Learn from other Founder’s Mistakes and Successes

“Entrepreneurship is synonymous with failure,” says Derek Andersen the founder of Startup Grind, a 150-Chapter community for entrepreneurs. “Great entrepreneurs probably fail more than anyone else but they relentlessly search for solutions while at the same time being unafraid of the consequences of short term failure.”

As unique as your startup may be, there’s likely been people in the trenches before you who have experienced many successes and failures. These entrepreneurs often are willing and eager to share their advice, talking openly and truthfully. Whether it’s an issue with customer validation, marketing strategy, product development or another issue, you’ll find someone in the ecosystem who has been there before you and achieved some milestone you dream of reaching too.

Discover Potential Customers

There may be an assumption that most people in the startup community are too busy building their own businesses and don’t have time to help others. In fact, many professionals get involved with startup communities to give back and include making connections among their own network. What you may find is the community is connected with larger businesses which may be your ideal customers. People within the community start referring customers to you that they think may be a great fit or perhaps become paying customers themselves.

Accelerate Your Startup Success with Venture Out’s Lab

Venture Out’s vision is to increase founders’ chances of success by providing a community of like-minded individuals, programming and mentorship to support your growth. Our Lab is a breeding ground for entrepreneurial-minded engineers and successful business minds building their next companies or seeking to join a fast-growing startup. With that passion and dedication, we offer a unique opportunity to connect with the startup community through the Big to Small Lab.

Learn more about our Big to Small Lab

“Winners quit all the time. They just quit the right stuff at the right time.” – Seth Godin

Difficult conversations are never easy. Especially when it comes to talking with your partner about a big decision like quitting your day job to pursue your startup. 

You’ve made the leap of faith to go all in and having your partner’s commitment and support on your new venture is important to start on the right foot. So having this difficult conversation is not only necessary before you take the leap but vital for your startup’s success.

Considering quitting your job to launch or join a startup? Learn more about our Big to Small Lab

Important Points to Bring Up During the Conversation

1. Communicate what the decision is and why you feel it’s best for not only you but your partner. When your partner clearly understands the why behind your decision and that you’ve looked at it from multiple perspectives, they’ll feel more comfortable with and involved in the decision.
2. Share your vision and commitment to the short and long-term plan including timelines for certain milestones to be accomplished. Having outcomes to measure the progress of your decision will help make course corrections when they arise. A CEO’s job is to articulate the vision of the company. Sharing your vision is good practice before doing this with potential co-founders, early hires, mentors, and investors. 
3. Explore what’s the worst-case scenario and discuss the contingency plans if it does happen. Leaving a steady financial stream of income is a big risk that many are not willing to take, so setting a clear contingency plan if certain milestones aren’t reached is key to moving forward with the big decision. This includes calculating your burn rate and startup runway to have a solid understanding of how long your cash flow will last. 
4. Allow space and time for your partner to ask any questions as difficult as they may be. Your partner will experience the ups and downs of the decision as much as you do, so ensure their concerns are heard and addressed. 
5. Express your appreciation and gratitude. Your partner believes in you and this unwavering support is crucial to get you through the many successes and challenges along the way. Ensure you express how much your partner’s dedication and commitment mean to you.
6. Check-in often. This type of difficult conversation doesn’t just happen once and is over. The depth of the conversation will progress as you and your partner will experience varying emotions during this new journey. Make sure you touch-base often on how your partner is doing throughout.

No one likes having difficult conversations. However, there are ways to turn difficult conversations into healthy, productive discussions where both you and your partner feel good about the outcome of quitting your day job to pursue your startup passion. 

Venture Out helps tech employees launch or join a startup.
Learn more about us here

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

I was running a brick and mortar direct to consumer wellness company that was piloted in Seattle with quick traction. We grew the firm into 17 partner facilities within 12 months, when the technology platform Thrv came to fruition after hearing the same pain points across all 17 of our facilities. While it wasn’t the crux of our legacy business, it was a solid platform to leverage data and deploy a go to market strategy and product validation for the SaaS solution.

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

I wanted to move toward a more data driven approach to business but never had the ability or knowledge set to immediately transition. There was a distinct moment driving to work when I realized…”I don’t ever want to HAVE to drive to work to actually work”. Having autonomy was one of the biggest factors in realizing I wanted to transition out of my legacy company so as to not be beholden to anyone else on their time frame.

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

Initially I knew what I wanted to do and knew how to get to that point…while ALSO knowing I did not have the tools to get there- yet. Not having a base in technology, adding a data play to work was daunting. I had all the typical negative self talk conversations with myself- until I met Sean and Venture Out.

Have an idea? Join Venture Out 

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 put in the notice…to myself. So it was the hardest decision as I felt I wasn’t seeing things to the end. Luckily I had the right people in place to make the transition as smooth as possible and still participate where needed.

5. What are you doing now?

This free time allowed me to focus on scaling the next iteration of Thrv Health, which is to scale the MVP and user validation outside of the immediate city of Seattle. I think it was important for me to “stumble” through the process of moving into a foreign industry (tech), so as to not take validation from my legacy company that was in the same market space- wellness. Just because we had a successful brick and mortar wellness company, doesn’t mean that translates to a tech platform in the least.

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 started being uncomfortable earlier in the process. Before going through Venture Out, I sat in a lot of meetings and workshops as a fly on the wall. Worried about the optics of my questions. Worried about the judgement of peers. Worried about looking…lost. But- after going through Venture Out and realizing we all start somewhere and uncomfortable is the name of the game in start ups….I wish I had asked the silly questions earlier. I couldn’t be more happy with this new chapter.

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

Find a good cohort and get uncomfortable. Get vulnerable. We all felt it at some point even if we don’t show it.

Venture Out helps tech employees launch or join a startup.

Learn more about us here

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

I was a software engineer for 5 years at Microsoft working on the Microsoft Authenticator app, Windows 10, account security, and the sign-in experience across all platforms.

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

Back in college, I took an entrepreneurship course where I started a company (a social app, obviously!) with a small team of fellow classmates. We ended up winning a few competitions and even got to pitch the idea to Shark Tank’s Robert Herjavec (he was only mildly impressed, unfortunately). Although the company fizzled shortly after graduation, I knew then that the startup world was where I wanted to be.

Post graduation, I decided to spend some time honing my technical skills at Microsoft. Over the next 5 years, I moonlighted as an aspiring entrepreneur, spending countless evenings and weekends exploring new ventures and jumping from one potential idea to another. But nothing quite had that “this is it” feeling.

This went on until, one day, I was introduced to my eventual co-founder, who was working at Alaska Airlines at the time. He had identified very real problems in the aircraft maintenance space that could use a better solution. Intrigued but knowing nothing of the aviation industry, I helped him build a proof of concept. Within a short time, we had a demo set up to show potential customers the idea – and I remember being completely floored by how excited people were to see our vision, which was really only a concept at the time. It showed me that there was a real gap and a real need for change in this space, and how much of an impact I could have. It was on that day that I knew it was time to take the leap. 

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

Did I ever have hesitations! Everything from losing my financial stability to entering an industry that I knew nothing about–I had a daily rotation of concerns that kept me up at night.

But there were two things that ultimately helped me get over the hump:

1. I saw with my own eyes how excited our future customers were about the proof of concept that we had built and how much they wanted us to continue building out the product. There was something uniquely satisfying and rewarding about having that experience, and I didn’t want to let them or the vision down.
2. After 5 years at Microsoft, I knew that I had gained enough skills to find another software job later, if all else failed. I also knew that I was going to learn as much as I possibly could with my startup and no matter what the outcome was, I was not going to leave the experience empty-handed. 

Have an idea? Learn more about how Venture Out can help you 

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, I was afraid to tell my manager that I was leaving to start a company–not because he would not be supportive–but because I did not want to look foolish if, after making such a grand departure, my startup crashed and burned. In hindsight, I was obviously in my head, but the feeling was very real at the time. Even though I didn’t tell my manager the reason I was leaving, he was extremely understanding and told me the door was open if I ever wanted to return. This gesture meant a lot to me and I am forever grateful to him and all my past managers for always being so supportive of my career and my decisions.

5. What are you doing now?

I am happy to say I just crossed the 5 year mark with Aerostrat and we are still going strong. As you can imagine, the pandemic has been trying for many of our customers, and we are incredibly grateful that they have continued to work with us through the tough times and continued to recommend us to others. 

For those curious, at Aerostrat, we built a web-based application that helps airlines and MROs (maintenance and repair organizations) very easily and quickly build a complete picture of their maintenance operations for many years into the future. It allows them to build budgets, forecast what-if scenarios, understand capacity requirements, and most importantly, automatically create a highly optimized and centralized production schedule of all their maintenance needs across their entire fleet.

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 had done a better job of keeping in touch with all my friends and all the amazing colleagues I met throughout my time at Microsoft. When starting a company, there is this drive to put your head down and build nonstop until you make it. But in a small company, you end up talking a lot to just a few people instead of the tens or hundreds you used to interact with. It can be isolating, and it was tough for me to regain those friendships. If I had the chance to do it over, I would work just as hard, but carve out time to stay in touch with others, and also find a good support network of other founders to bounce ideas off. You have to become an expert in so many areas when you’re part of such a small team that any help can really make a big impact. 

While the journey has not always been easy, I have no regrets. There is something very special about building a company from scratch and seeing how happy your customers are every single day. I know I am making a difference and that has made it all worth it.

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

I would recommend two things:

1. Talk to others (especially other founders) and just make sure you understand what kind of journey you’re about to embark on. It isn’t for everyone and it can be an emotional and stressful rollercoaster.
2. Once you understand what you’re about to do and think you have a great idea, dive headfirst and don’t look back. Startups require everything you’ve got, and looking back will only slow you down. Just know you will come out stronger, especially with failure, and you will be better for it.

There is no better time to be a startup founder than now. There is more capital available, there are more VCs to give you their money, access to software is cheaper, and there are more accelerators, and incubators to support you than ever before. If that is not enough, startup valuations are at all-time highs and employees from big tech are leaving their day jobs to pursue startups at a faster rate than ever before.  

So, if you are an employee holding a tech day job the question becomes, are you better off to VIP (Vest in Peace) while earning your RSUs or build the next company as a startup Founder?  

While there is no better time to be a startup founder and there are more resources available than ever before, most employees at big tech companies do not know where to turn to for funding or know-how to validate their startup idea, let alone know where to find a vetted network of mentors to support them.  

It’s understandable.  Like many of us, we landed in Seattle without an established startup network. We had a craving to be around smart, ambitious people who wanted to make a positive impact, but we didn’t have the startup network locally.  We were too busy in our tech day jobs to build our network but after months and months, we earned the trust and support of so many amazingly talented individuals.  Now we are here to support you, the next wave of talent entering the startup ecosystem.  So, whether you are crushing it at your day job or dreaming about building the next great startup, we’ve got your back and are ready to connect you with an amazing group of people to catapult your startup network and expedite your path forward so when you do cut the cord, you can hit the ground running.

We took our experiences, tested it on tons of participants, iterated on it, and then got buy-in from some of the best VCs in the Seattle area to invest in it.  Now we offer you the ‘Go Big to Small’ Lab.  It’s 10 weeks long (part-time while you keep your day job).  You’ll gain the frameworks to launch a startup, build a 100-day plan to execute your startup’s vision, and meet over 100 startup founders, mentors, technologists, venture capitalists, and more stemming from the Pacific Northwest to deliver you a top-tier startup network.  This lab is dedicated to those seeking to engage with other smart, ambitious technologists seeking to launch a startup or work for one in the next six months. We can’t wait to meet you.

Venture Out helps tech employees launch or join a startup.
Learn more about us here

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

I was a senior director of product management at Microsoft Azure. My organization’s last mission was to revamp how Azure builds its data centers and cloud regions to make them more resilient to failures. This was one of the top enterprise requests from customers looking to build mission critical applications on Azure. I was lucky to partner with very talented people on this journey as we changed Azure from soil to its core services.

Prior to Microsoft, I was an early product management hire for AWS where I defined and built the businesses around many of the AWS developer services. One example of this was S3, which I helped grow into an exabyte-scale service used by some of the largest enterprises in the world.

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

In 2015, I started investing in real estate and learning about how to effectively buy and manage rental properties. I experimented with DYI management vs. property management, short term vs. long term rentals, and flips. The more I dug in, the more I realized that investing in real estate is hard and requires lots of manual tasks, especially for people who work outside of real estate. My itch to solve these problems with software kept growing every day and other real estate investors confirmed a similar set of problems and stories. In 2019, I just couldn’t shake the feeling that my true calling was to use my product development and management experience to make an impact on real estate investing space. This was the genesis of Padvest.

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

When leaving a steady job, I felt all the usual discomforts: worries about the loss of financial stability and health benefits, the anticipation of more stress on myself and others around me, and the fear of failure. I was lucky enough to be surrounded by supportive friends and family who encouraged me to think about these as “solvable problems” rather than “hesitations”.

I wrote down every nagging discomfort and worked out a potential solution for each of them. For example, to support myself financially I created a tiered approach for how I save and spend money.  I reduced some of my largest expenses, and even started a business to help bring in additional income. There are many ways to go about solving each of these problems and I am always happy to pay it forward and help others brainstorm.

Have an idea? Join Venture Out 

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 last day was very bittersweet and emotional. On one hand, I knew I was going to miss working with my team and partners. On the other hand, I was excited for my new journey. My mantra for these moments is best represented by the French expression “au revoir”. It translates to “until the next time” and it leaves the door open for a reunion at a future time.

I’ll share a few mind tricks that helped me get through the day:

• Morning workout routine
• Meditation with a focus on gratitude for past times and a hope of reuniting with my teammates in a new setting
• Farewell hallway conversations
• Lunch with a few people
• Spotify playlist on repeat on the drive back home with a mix of dance music and rock music to get those good vibes
• Bright spot: I wasn’t going to miss 520 rush hour traffic
• Nice dinner out with loved ones

5. What are you doing now?

I am now building Padvest, a real estate investing platform that helps investor research and manage their residential investments. We launched our first product in 2020 which helps people evaluate investment properties in seconds using a powerful data platform that aggregates data across many sources. Our mission is to empower every person to generate wealth through real estate investing. I am very excited to wake up every day and continue building out the team and expanding our portfolio of products that contribute towards this mission.

If you are interested in working at a startup, if you share a similar passion for our mission, or if you are a real estate investor, please reach out to me. I am always looking to connect, as we continue to build our team and products in support of our mission.

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?

Building a startup is a continuous growth and learning journey and if nothing else, that is enough to make me happy. Of course, getting love notes from customers and seeing your user base grow, feeling proud of what the team has built, and knowing that we are making real estate investing more accessible all add to that feeling of satisfaction. I would make the same decision again in a heartbeat.

When transitioning from the corporate world to entrepreneurship, I did not realize how many support and back-office systems I took for granted in a corporate environment. For example, most corporations already have marketing and content platforms, a sales process to engage with customers, and HR systems to support employees and managers. When building a startup, it’s easy to think that you either need to build these things or pay a fortune to outsource them.

What has surprised me is the amount of tech platforms and automation that can help you bring these functions to your startup quickly, in an on-demand, follow-your-growth fashion. I highly recommend that each entrepreneur asks others for recommendations when it comes to building these systems. As an example, we used an automated legal platform to set up the company and manage much of the initial paperwork, with the help of a lawyer as a reviewer. We were able to move fast and keep our legal costs down.

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

Don’t be afraid to ask for help. In my one and half year of entrepreneurship, I have been incredibly surprised by and grateful for all the mentors and community who have helped me and Padvest along the way. Reach out to people, ask for connections, and be genuinely curious. There is something to learn along the way and always offer your experience back. In fact, I would love to pay it forward and help new founders as much as possible too. If any of my journey or Padvest’s mission resonate with you, don’t hesitate to reach out!

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

I worked at Microsoft in Product Marketing. I joined Microsoft at 24 and spent a decade working in various Product, Sales and Marketing roles. When I joined, we were selling Windows Vista via CDs to our customers. This summer Microsoft announced Windows 11 in the Cloud, almost 14 years later. The innovator’s dilemma is real. I got a first-hand education through many Windows launches just how hard it is to innovate and upgrade billions of customers to the cloud.

I spent most of my career in Windows incubating new products, running pilot and enterprise adoption programs and most recently on Google compete strategy. I learned a ton in that time that has served me really well in startups. I think some people have the idea that Microsoft employees aren’t agile enough to run startups. That couldn’t be further from the truth. One of my greatest strengths as a Founder is my ability to build, pilot and sell enterprise software. As a non-technical Founder, this has served me well as we’ve been able to commercialize our product much earlier than most startups.

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

As I was approaching my 10-year anniversary, something totally unexpected happened. As if overnight, purpose vs. money became a more important driver for me. I remembered a promise I had made to myself back in college when I decided to double-major in Business (I was already on track to receive my Anthropology degree). I remember telling myself that I would go into business to get “money, influence and power” and then use that privilege to make a difference someday. At that moment, I realized that I’d spent almost a third of my waking life working for Microsoft and that the time had come for me to apply myself to something more purpose driven. 

I didn’t immediately quit my job. To be honest, I never thought I’d leave Microsoft. I left 15 months later; but not before being involved in a freak skiing accident with my new boyfriend (now husband) two weeks before my end date. I was hit by a snowboarder from behind with such force, I immediately tore my ACL, fractured my tibia, ruptured my meniscus, and tore my posterior lateral corner. As I was falling down the mountain in slow motion, I remember thinking, “What have I done?” followed by “Thank God I still have insurance.” I was scheduled to speak at several pitch competitions and conferences in the coming weeks. I was tobogganing down the mountain in tears as I faced the sobering reality that I’d need to learn to walk again, in addition to navigating the uncertainty of startups and life outside of Microsoft.

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

Money! I was single living on a houseboat on Lake Union in Seattle. My mortgage + moorage wasn’t insignificant, and I worried how I’d be able to afford my lifestyle if I quit. I had saved 6 months of living expenses and told myself that I could always go back if the money dried up. Indeed 6 months later I was given the opportunity to do some consulting work which allowed me to continue building Tribute. At some point, you have to trust your gut and take the leap. I had many hesitations about quitting, including what my friends and family might think, but ultimately, the idea for Tribute was too powerful to not go for it. As silly as it sounds, I knew it was my calling and that I needed to follow it. Thankfully, I feel like Microsoft would welcome me back with open arms if I ever wanted to go back. Without a doubt, I’m a better employee today for having the education that startups have taught me.

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 was a cold December day. I had been ideating on Tribute for over a year. I found that more of my thoughts and time were being spent on Tribute vs. my day job. I knew then that it was time. My integrity wouldn’t allow me to keep accepting a paycheck from a company I wasn’t giving 110% too. As I drove in, I felt a lightness of being that reaffirmed my decision. My manager was admittedly disappointed but not surprised. I had been open and transparent with him from the beginning. He took it great and fully supported my decision. Rather than a standard two weeks’ notice, I stayed on for another 3 months to help recruit my replacement and do a full transition. I keep in regular contact with my old team today and have leaned on their support, including my former Manager, more times that I can count.

5. What are you doing now?

Tribute just turned two and is thriving! We’ve got several enterprise customers today, including Microsoft, have raised capital, grown the team, and are just getting started. I sold my houseboat, got married, moved to Ballard, had a son, and have another one on the way. Building babies alongside businesses is another blog post all together! 

The pandemic had a silver lining in that remote work has really challenged how we make meaningful connections in the workplace. Tribute’s peer-to-peer mentorship app, available in Teams and Slack, is perfectly positioned to help companies attract and retain top talent in this new hybrid work era. Investments in HRTech are booming as we’re all reimagining the future of work. Tribute was also selected as one of the only female-founded startups to be included in Microsoft Viva’s launch at Inspire in July.

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?

So many things! Learning to tell your Founding story (your why) is critical when venturing out. Most people don’t know how to make sense of someone in their mid-30s leaving a stable career to start a company. Being able to communicate your mission, your why and why you are the one to lead this mission is critical. In the early days investors are betting on you. Without a compelling story, it’s going to be hard to build the momentum you need to get your idea off the ground.

I’ve grown so much in the years since venturing out. There are hard days when I question everything, but ultimately, I’m very happy with my decision. I’m a better person, employee, wife, Mom, friend for having this experience. Plus! Tribute has helped thousands of people all over the world find a mentor. Finding a Mentor can be life changing and I know our mission is making a difference in people’s lives for the better.

No matter what happens, I know that finding the courage to follow my calling is serving others, and that is always a worthwhile pursuit.

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

Venturing out is scary, but so worth it. If you’re considering a similar path, my advice is two-fold. First, I would find a mentor (aka someone who has walked this path) and ask as many questions as you can about what to expect. Second, don’t quit your day job too soon. Running a startup is a marathon, not a sprint. You’ll want to time your exit correctly, so you have the runway you’ll need to succeed. In startups, it’s not enough to have a good idea or even a good product. You need to have a good business in order to succeed out here. Leaving because you have a good idea is almost surely to run you into the ground before you have a real chance to begin. If you’re a female founder, join the Female Founders Alliance run by Microsoft alum, Leslie Feinzaig. That community of founders has been a lifeline to me throughout my journey.

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

I’m a former Amazonian. I worked as a legal specialist. I was highly involved with other teams on the philanthropy side of Amazon, specifically with the Disaster Relief sector. 

While working at Amazon, I co-founded Puerto Rico We Care, a 501c3 nonprofit organization that provided disaster relief to Puerto Rico after it was devastated by hurricane Maria in 2017.

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

After working in philanthropy and co-founding a nonprofit, I fell in love with this sector. To explain my inspiration, I must go back to where it all started – Puerto Rico. 

Back when the hurricane devastated Puerto Rico, people in the mainland wanted to help. Over 200,000 families lost their homes, 4,000 lives were lost, and the island was without power for almost a year. It was a desperate time. When people in the mainland began sending aid, the Puerto Rican government implemented lots of red tape. It was disorganized. A group of us in Seattle came together to use technology and help expedite aid. I designed and created a platform using Amazon Wishlist’s. Donors could easily choose which items they wanted to donate, and their donation would arrive in a matter of days. In Puerto Rico I had over 100 volunteers in the 78 towns that make up the island, and they would distribute to families in need. In a 2-month period over 300 donors donated over 20,000 items and impacted 4,000 families. This was one of the many projects we worked with at Puerto Rico We Care. 

After our project ended, many nonprofits came to talk to me to understand how they could replicate that success. Right then, I understood that there was a big gap between the nonprofit sector and technology, and I wanted to close that gap. I began efforts to bring better technologies to Amazon to help improve the nonprofit sector, but my ideas were too big at that moment. I decided that my time would be better used by creating a new platform for the nonprofit sector and departing from Amazon.

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

As many first-time entrepreneurs I think the first thought is – “am I crazy?” But then it’s followed by “In a few years, am I going to regret not going for it and say “What If?””, “If not now, when?”, “If not me, then who?”

Yes, working for one of the best companies in the world is rewarding. Yes, the money was good. But there’s no feeling more incredible than creating your idea, launching it, seeing it live, watching it grow and most importantly – changing people’s lives. 

Did I have questions? Yes. Did I have hesitations? Never.

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 remember that day like it was yesterday, and I think I will remember it forever. I was nervous, anxious, but above all, I was excited. I can’t talk for my former manager because I don’t know what was going through her head. All I can say is that it came in as a surprise.

5. What are you doing now?

I’m the founder and CEO of NEDDIE. 

NEDDIE is a nonprofit marketplace where nonprofits and donors can easily connect, engage, and support the causes they love. 

It has been an ongoing hurdle for people to find where to help, and for nonprofits to be exposed to new donors outside of the same loyal donors they’ve had for years. Time is money, especially when that money is to cause change. People want to help but they want to do it in a fast, easy, secured, and simple way. With NEDDIE, donors are empowered to easily find nonprofits, engage in a multitude of ways, and track their donations. 

Finally, nonprofits have a hub where they are constantly exposed to new donors and can create new long-lasting relationships. We have over 40 nonprofits on our platform from WA and Puerto Rico and plan to expand nationwide. 

Some people call us the “Amazon of Nonprofits”. We are just happy to have a place for nonprofits where they are at the center stage. NEDDIE is the new hub for being part of philanthropy and creating meaningful connections. 

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?

Many know that founding a company is not easy. It is a rollercoaster of success and emotions. Sometimes your company has great momentum and is performing amazing, other times you feel like you are filling holes in a sinking ship. Ultimately, it is up to you to keep pushing, move forward and take your company to the successful path that you’ve envisioned. 

I don’t think I would’ve wished to know more about the entrepreneur path before I started it. Maybe I would’ve thought it was a big risk or that I would’ve questioned my knowledge, and I might have feared to move forward. Instead, I took the leap and I trusted in myself. Throughout my journey I’ve been learning so much from other entrepreneurs and investors. I’ve fallen hard and I’ve learned how to get up, and with that I’ve become a better CEO and founder for my business. I’m not only happy with my decision, but I’m also proud. I’m a very different person now than when I was in front of my computer designing NEDDIE for the first time.

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

Do It! Do you have a great idea? Share it with the world! Your idea might be the key to improving people’s lives. If you have doubts, ask yourself “If not me, then who?”, “If not now, when?” It is a risky business, overwhelming all the time, and it keeps you at the edge of your seat. But if you have a passion, if you have a dream, if you are willing to give it your all to make it happen, then trust in yourself and go for it. I believe that:

– Mentorship. Having mentors and a support system is the key. 

– Networking is important! Don’t be shy, ask for help. Your success will be possible not only because of you, but also because all of those who are helping you build that ladder going up. 

– Listen. Learn from others that have paved the path. Don’t be scared to hear something that you don’t want to hear. When needed, listen, adapt and pivot. Making tough decisions will be part of the process.

– Finally, be a good leader. Companies are built by people, not just one individual.

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

I was working as a Software Engineer at Karat, a Seattle-based startup that conducts technical interview screens for rapidly growing engineering teams.

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

At the beginning of the COVID-19 pandemic I was stoked to work from home for 2 weeks. I’m an introverted Software Engineer– this will be awesome! I was really excited to work in my pajamas and spend more time with my rescue dog!

But, after 9 months of isolation from my colleagues, friends, and family… the excitement disappeared. Before resigning I actually took a couple weeks off for mental health. (I am incredibly thankful to have been part of such a supportive team!) I officially resigned in late October 2020 (before the election because that was another huge element of stress) and spent 2.5 months completely recharging, focusing on self development and learning.

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

– Financial stability: I made sure I had a good cushion of savings and knew my monthly burn rate. We also decreased our rent by moving outside of the city.

– Health insurance: I knew getting health insurance was crucial during a health pandemic. I ended up keeping my insurance through COBRA and later switched to a public market plan.

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 was very supportive as was the rest of my team. (Karat is an awesome company to work for and are actively hiring for many roles.)

The day I gave notice I felt a huge sense of relief. I knew I would have time to just live and survive through the pandemic without daily job responsibilities. Entrepreneurship and starting my own company has always been my end goal, but I didn’t know how soon it would be coming my way!

5. What are you doing now?

I am now the CTO & Co-Founder of HelloPrenup, the first digital platform for couples to seamlessly create prenuptial agreements. 

HelloPrenup makes obtaining a prenuptial agreement affordable, fast, and easy! Everyone who gets married has a prenup, they may not know it yet. Those who do know it, realize how difficult and expensive it can be to draft a prenup. It shouldn’t be so hard! HelloPrenup is the first online platform to offer valid prenuptial agreements created using smart algorithms, offered at less than a third of the cost of a typical prenuptial agreement, and requiring a fraction of the time it takes to draft a prenup through attorneys. 

HelloPrenup charges a transparent, flat rate fee of $599 per couple for a prenuptial agreement, and the process takes about 2-3 hours from start to finish, whereas attorneys charge $2,500 per individual, on average, and the process takes 3 months!

Why a prenup in the first place? Through the use of prenuptial agreements, anyone can protect their financial interests and avoid potential economic pitfalls that can befall many married couples by controlling what happens to pre-marital property, business interests, change in income, among many other factors.

Use discount code VENTUREOUT for $100 off your prenup! (Expires 08/01/21).

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 never worked on a direct B2C product. Many Software Engineers think that if you build a good product, people will come flocking to it. But people can’t use your product if they don’t know it exists!

SEO and online marketing were completely black boxes to me. I have learned so much about the importance of content and online presence for building a consumer focused business.

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

Find a Co-Founder that is an expert in the industry you are looking to innovate in (especially if you are the technical Co-Founder!) 

In February 2021, I recognized the need for innovation in the prenup market– millennials are getting engaged and we demand modern solutions for everything we do! The traditional prenup process of vetting 2 divorce attorneys, paying uncapped hourly rates, and waiting months… all while planning a wedding… is the opposite of what we want! 

As a lone Software Engineer I knew I would either need: a Legal Co-Founder or a Legal Advisor to make my vision possible. While conducting competitor research, I came across HelloPrenup and reached out to Julia Rodgers, HelloPrenup’s CEO and head of Boston’s premier family law firm. (Advice: as an entrepreneur you really have to get over any fear of cold emails or phone calls!) It turned out that our visions to disrupt the prenup space aligned perfectly! With Julia’s legal and my technology expertise, we have grown the business exponentially since teaming up in March 2021.

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

 I was the VP Connections at Amazon.

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

I have been mentoring young women in STEM for my entire career, but I could only help one woman at a time. I wanted to create a scalable platform that could offer insightful career advice to STEM women regardless of where they lived in the world. I didn’t have a eureka moment where I thought, ‘Okay! Today is the day I quit my job!’  It was a dream I had been nurturing for some time, and, like any great passion, it grew to the point where it couldn’t be ignored. And it was perfect timing from the market perspective. That’s when I knew it was time to scale what I describe as my second [career] mountain. Leaving India to do graduate work in the States and building my professional career here at Nielsen, GE Aviation, and Amazon was the first mountain. It was a fantastic hike, but Gotara is a whole new beautiful landscape to explore.

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

Like anyone, you can get used to the routine of having a job that is intellectually and creatively fulfilling. Still, in my life, I have always tried to resist becoming too comfortable and coasting in a role. I like to have butterflies in my belly; that delicious mix of facing the unknown but also knowing that’s the way I want to lead my life because of the rich adventures it always leads to—like Gotara. 

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 loved my time at Amazon, so the day was a mix of emotions, but it felt like I was running toward a new challenge. You don’t get to experience those moments often in life, so you have to seize them. I had already prepared my manager for a change almost a year before.  She was supportive and intrigued, and her curiosity gave me an added boost of confidence that this was the right time to make a move. 

5. What are you doing now?

I’m climbing that second mountain and loving every moment. There’s been a few times when the climb seems a little too steep, and the path is uncertain, but Gotara’s mission is so clear, and my dreams for it are so vivid that I catch my breath and dive back in. I’ve created a virtual global team who all share this dream to create this platform because we know it will change women’s lives. And given the hit STEM+ women have taken during the pandemic—Gotara’s purpose is even more poignant. We’ll help women get back on their feet and back in the game. The advice, support and key learning moments we share with them will be life-changing. They’re not the only ones who benefit. Employers have engaged employees and the inventions these brilliant STEM women imagine will make all our lives better.

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?

Good question. If I had a proverbial crystal ball, I might have made some different decisions earlier on in terms of how and when we might deliver specific services, but having to pivot exercises one’s innovation muscle, and that’s a good thing. We’re constantly examining how and why we do things and if the process can be improved. I’m content with the decisions we’ve made—and proud of how we have innovated around moving goalposts.

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

It isn’t for the faint of heart. You have to know what you want; and have a North Star vision that keeps you on course. Be open, curious and have enough humility to know when to trust your team and be open to reevaluating a decision or changing direction. There will be tough days; you’ll have to make tough decisions but our tagline at Gotara is #spiralup. It’s also my mantra in life because I’m wired to reach for the stars. 

Learn more about Gotara here