Small Market Startup
By Kyle McLeod
Small Market StartupOct 17, 2022
Chasing the dream with passion and persistence with Jason Wiener
Welcome back to another episode of Small Market Startup, where I’m exploring the dichotomy between startup success and quality of life, with a specific focus on growing a business and living in a smaller market (like Bend, OR where I’m at now). This week I interviewed my friend Jason Wiener, Founder of Hyperdrive, currently the Vice President of Product and Engineering at Blueboard, and a friend to all startups and tech business in Central Oregon through his spot on the board of BendTECH.
Today we get into his history of building businesses, working for himself for 25 years, and turning himself from a marketing major into an incredibly technically proficient founder who has a passion for solving hard problems. We round out the episode by diving a bit into startup life here in Bend and how to make the best of every situation you may face on your journey.
Listen on for some awesome life lessons from someone who has been through so many changes in life and figured out a way to make the most of every challenge and opportunity that has come his way. I know I learned a lot and I hope you do to... Enjoy the show!
Sponsor section!
This week is sponsored by… me! And some great groups here in Bend for building your network. You can find them both on Meetup.com and our slack channels here:
https://www.meetup.com/bend-startup-central/
https://www.meetup.com/bendjs/
And as always, if you want to be on the show, sponsor the show, or have any questions, please reach out to me directly at kyle@cloud99designs.com! Thanks for listening
Chris Bailey - Exploring the outdoors and life of a successful entrepreneur
Welcome back to another episode of Small Market Startup, where I’m exploring the dichotomy between startup success and quality of life, with a specific focus on growing a business and living in a smaller market (like Bend, OR where I’m at now). Today I interview Chris Bailey, Co-Founder of HotelTonight which sold to AirBnB in 2019 and current Co-Founder of NatureQuant. During the interview today we go deep into Chris’s backstory and how his drive, ability to connect with others, network and make close friends, and his technical expertise has led to an incredible career that’s still on the rise.
In so many ways, Chris is my idea of a unicorn, and what I’ve been chasing with this show. He’s a successful multi-time founder who truly believes in the power of balance and keeping quality of life a high priority, even when chasing success. His new company, NatureQuant is a prime example of his passion for the outdoors and making sure you take your health and overall quality of life into consideration in everything you do.
Listen on as we go through his history, through advising startups and lots of great technical work he’s done, through his time at HotelTonight, and moving onto his new venture. Throughout it all, Chris provides some incredible insight into the power of hard work, networking, and keeping everything in perspective. Enjoy the show
Sponsor section!
This week is sponsored by… me! And some great groups here in Bend for building your network. You can find them both on Meetup.com and our slack channels here:
https://www.meetup.com/bend-startup-central/
https://www.meetup.com/bendjs/
And as always, if you want to be on the show, sponsor the show, or have any questions, please reach out to me directly at kyle@cloud99designs.com! Thanks for listening
Starting a talent agency with Jamie Ceglarz
In this episode I interview Jamie Ceglarz, the owner of Guild Talent about his journey to starting his own company, moving from SF to Bend, and living the good life with his family. We also dive into how employees are thinking about their jobs and their quality of life and what employers need to consider when trying to find the best talent. If you're looking for a job and you're a high performer, you can find Jamie at GuildTalent.com or email him at Jamie@GuildTalent.com
Finding Passion and Balance in your Career - With Shelley Kay Coaching
In this episode I discuss finding passion and balance in your career with Shelley Kay. Shelley is a coach for career driven women, and although she isn't specifically focused on the startup space, I found her perspective to be incredibly enlightening and think that her tips and coaching strategy can help just about anyone trying to find balance between work and life, and figure out ways to reignite the passion they have for life.
Exploring a Founder's Journey with Noah Abelson-Gertler
Welcome back to the Small Market Startup podcast. On this weeks episode I interview my buddy Noah Abelson-Gertler, co-founder of ShareRoot and currently focusing on coaching founders and co-founders through his company, A Founder's Journey. We dove headfirst into his own journey as a founder of a company that went public on the Australian stock exchange, what is was like going from 0 to public and some of his regrets about how it all went down, and how that led him into his current mission of helping founders navigate the choppy waters of starting and growing a company. I wish I had more time with him for this interview and there is a lot we left on the table, but I'm holding him to a follow up interview in the future, so stay tuned for that. Now let's jump into the interview...
Getting to know Erik Pearson of Occupier.com - Running a business from NYC to Bend, OR
In the second episode of Small Market Startup I interview the CTO and co-founder of Occupier.com, Erik Pearson. Erik recently moved to Bend after exploring the country a bit, but started on the east coast in NYC where he helped build Occupier with 2 friends. Erik brings a very interesting perspective to the show with his experience as a co-founder, but being on the technical side he's mostly been shielded from the intricacies of dealing with investors on the regular. For Erik it all comes down to company culture and being able to live his best life while continuing to grow at a great clip, and from his perspective, getting lucky with great Investors like Occupier has allows that dynamic to flourish. It was a great interview and we're excited to bring another great founder to our town. Enjoy the episode.
Exploring tech and building a business with Chris Coyier of Codpen.io
Welcome to Small Market Startup, where I explore the relationship between success and quality of life (I think you can have both) in the startup ecosystem. My name is Kyle McLeod with Cloud99 Consulting where I do product consulting with tech startups. As I'm getting into building my own startup and even exploring the edges of the VC and investment world, I wanted to explore the pressure that I've heard traditional VC incentives put on startups. I have a family and love my quality of life here in Bend, OR and want to know that it's possible to bring that culture to a business and still have success without being beholden to 80 hour weeks and no life outside of work.
This show will explore that by doing interviews with a wide range of stakeholders in the startup ecosystem and we'll see if I'm right or if the traditional path is still the best way to go.
This first episode is with my good buddy Chris Coyier of Codepen.io, CSS Tricks and the Shop Talk Show podcast. Chris has been through quite a journey to get to where he is now. I sure learn a lot from him every time we talk and I think you will too. Enjoy the show!