Neil Patel

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In the realm of startups, few narratives are as compelling and instructive as Kris Bliesner’s journey. With a career from early-stage ventures to navigating hypergrowth and transition periods, Kris offers a wealth of insights into the dynamics of building and scaling businesses.

In this captivating interview, Kris shares his experiences, challenges, and triumphs, offering a roadmap for aspiring entrepreneurs and seasoned professionals. He talks in detail about founding three companies and evolving six in all.

Listen to the full podcast episode and review the transcript here.

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The Ultimate Guide To Pitch Decks

From Washington State to the Startup World

Kris Bliesner’s journey begins in the scenic backdrop of Washington State, where his passion for technology and business management found fertile ground.

After college, he made the leap to the bustling tech hub of Seattle, immersing himself in the startup ecosystem while also gaining invaluable experience at Microsoft, working as a consultant contractor.

Kris remembers wanting to “scratch the technology itch” since he had studied computer science in school but was more interested in the business management side than the actual physics aspect.

Kris’ early exposure to the convergence of technology and software development on one end and business and accounting on the other laid the foundation for his entrepreneurial pursuits.

The Thrill of Startup Ventures

For Kris, the allure of startups lies in their capacity to break barriers and pioneer innovation. His foray into the startup world began with Shop.TheGlobe, a company amidst the fervor of the late 90s tech boom.

Here, Kris experienced firsthand the excitement of working on cutting-edge technology and the camaraderie of a tight-knit team pushing boundaries. He thoroughly enjoyed the transitions from business or corporate development to CTO, switching to and from the business side to the technical side.

Navigating the transitions wasn’t without its challenges for Kris. However, he recognized the importance of gaining diverse experiences to manage technology teams effectively.

He underscores the value of walking in the shoes of engineers, testers, and project managers, which ultimately shaped his leadership approach.

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Lessons Learned: Innovating and Selling Parkingeye

As the CEO of a technology firm, Parkingeye, Kris learned a lot from managing budgeting to P&A statements and building new things, especially when its product was ahead of its time. The story of Parkingeye exemplifies the highs and lows of entrepreneurial ventures.

The technology they had developed was to automate parking lot attendants. At the time, parking lots had slots where users could pay in dollar bills. Later, an attendant would come along and collect the money in the cash-based business.

Parkingeye developed machines that had a camera integrated into the pay station, which helped cut the labor out of the system. However, folks were just not interested in going out to purchase the pay stations and cameras and preferred to run the business as is.

While the technology was groundbreaking, Kris and his team faced the uphill battle of market readiness. Despite its eventual sale and success in overseas markets like the UK, ParkingEye’s journey illuminated the critical factors of market timing and customer adoption.

Kris recalls how the firm grew to more than $100M in the UK since the market was ready for it. The UK was already doing license plate recognition technology, so the concept of automated pay stations was easy to adopt. The market in the US was perhaps a decade behind.

Kris learned essential lessons on taking an idea through to production deployments, bringing in revenue from customers, and all the critical aspects of building a business. Looking at them from the founder’s aspect was an eye-opening experience.

Kris realized why a lot of businesses struggle to get off the ground because launching a product is an art. Finding customers, partnering with them, and getting them to pay for the product is extremely challenging.

Microsoft Interlude: Balancing Stability with Innovation

A stint at Microsoft provided Kris with stability and a deeper understanding of enterprise software development. He remembers being confident of his capabilities and what he could bring to the table at Microsoft.

Kris had some fantastic opportunities thanks to the teams and managers he worked with there. He recalls the significant learning curve he experienced in terms of software development from a large company perspective. And developing and launching some great products.

However, the pull of entrepreneurship remained strong, prompting him to venture back into the startup landscape eventually.

Building Ambassador Programs

Kris went on to build Ambassador Programs, a student educational travel program that gave college credits to overseas kids for representing junior high and high school. The company also started experimenting with the concept of the cloud.

They did intensive marketing campaigns once a year, which lasted for three months. At the end of it, they had built exceptional computing power and a huge data center with a secondary data center in Seattle for backup.

Kris and his team realized that they had the gear sitting there unused for nine months of the year. Next, they leveraged Amazon’s global footprint and started experimenting with ambassadors. It worked well for some of the workloads, so they built a business plan for using it without having the infrastructure.

However, running a data center came with challenges because, as a non-tech, small company, they had to have a lot of specialty skill sets. They were working with 20 or 30 different vendors, which could collapse into a single vendor.

The shift in the technology landscape was much like the mainframe and client-server. Leveraging the Amazon customer support desk, they looked at many forums and realized they had an innovative business idea on their hands.

It would be much more economical for non-technical businesses to have their data centers run on Amazon. The dynamic model doesn’t exist on-prem but only in the public cloud, so the business model has changed. Inspired by this idea, Kris and his team went on to establish 2nd Watch.

2nd Watch: Pioneering Cloud Migration

2nd Watch emerged as a response to the burgeoning cloud computing market, offering innovative solutions for data center migration. Kris’s strategic vision and industry expertise propelled 2nd Watch to become a leading player in cloud services well before Microsoft and Google caught on.

Kris recalls how they quickly became Amazon Web Services’ go-to partner. They did some of the largest data center migrations into the public cloud that have ever been done for brands like Coca-Cola, Nike, Starbucks, Toyota, Adobe, and Thompson Reuters, to name a few.

2nd Watch also did the first worldwide data center migration, where data centers in the US, Sydney, and Europe were moved all at the same time into the cloud. Kris remembers how he raised $40M across three different firms, including Madrona Venture Group, Columbia Capital, and Top Tier Capital Partners.

Next, Kris migrated the business from a technology company in general to more of a professional services managed services business. He also brought in a CEO and an additional $30M in funding before exiting in 2017.

Vega: Bridging the Gap in Cloud Optimization

With Vega, Kris set out to address the gaps in cloud optimization, leveraging his experience in managed services and cloud reporting.

By combining operational expertise with automation, Vega aims to revolutionize cloud management, offering a comprehensive platform tailored to the needs of enterprise clients.

As Kris explains, with Vega, he wanted to align reporting and operations. They started working out how to bring their capabilities of running a managed service provider and combining them with reporting capabilities.

They built a platform designed from the ground up as a large, multi-cloud-scale enterprise, but they were also trying to navigate the security landscape. CIOs and CSOs had to buy multiple tools to protect their environment. Vega allows them to integrate the tools on the cloud optimization side.

Kris explains how he raised $11M for the company starting with a friends and family round similar to what he did for 2nd Watch. Since they were operating within the same vertical, they were able to leverage repeatability, which made it easier for them to raise funding.

By securing strategic investments and fostering a customer-centric approach, Kris steered his venture through the complexities of scaling while staying true to the core mission.

He estimates that the market is worth $400B and is likely to grow to $1T in the next seven years, and that’s the market they serve with infrastructure and platform as a service.

Storytelling is everything, which is something that Kris Bliesner was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here), where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

Customer Focus and Revenue Realization

Reflecting on his experiences, Kris emphasizes the importance of prioritizing customers and revenue realization.

By aligning business solutions with genuine market needs and forging meaningful partnerships, entrepreneurs can lay a solid foundation for sustainable growth and success. Vega also saves its customers 25% on average, as Kris reveals.

In conclusion, Kris Bliesner’s entrepreneurial odyssey offers invaluable insights into the dynamics of startup ventures, from inception to scale. His journey is a testament to resilience, adaptability, and the unwavering pursuit of innovation.

As aspiring entrepreneurs embark on their own paths, Kris’s story serves as a beacon of inspiration and guidance, illuminating the path to entrepreneurial success in a rapidly evolving landscape.

Listen to the full podcast episode to know more, including:

  • Prioritize customers and revenue realization to anchor your startup’s growth trajectory.
  • Embrace diverse experiences to lead technology teams through innovation and adaptation effectively.
  • Market timing and customer adoption are pivotal for startup success, highlighting the importance of readiness and receptiveness.
  • Strategic partnerships and investments are essential for navigating hypergrowth and scaling ventures effectively.
  • Bridge the gap between reporting and operations to optimize cloud management and drive efficiency in enterprise solutions.
  • Stay true to the core mission while fostering a customer-centric approach to build trust and drive sustainable growth.
  • Entrepreneurial resilience, adaptability, and unwavering commitment are the cornerstones of navigating the startup journey amidst challenges and triumphs.



For a winning deck, see the commentary on a pitch deck from an Uber competitor that has raised over $400M (see it here). 

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The Ultimate Guide To Pitch Decks

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

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Neil Patel

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