We recently connected with Jayson Koss and have shared our conversation below.
Jayson, looking forward to hearing all of your stories today. Would you say you are more focused on growing revenue or cutting costs? We’d love to hear how you think about these two critical drivers
Depends on the time and goals of a company. Are you trying to sell, if so what’s taking place in the market / dictating highest multiples, ebitda or growth? There usually is a holistic balance between the two but when the table is hot you have to be ready to sacrifice some profit for growth and inversely when growth gets tough you may find yourself focusing on bottom line. Is the business a startup, raising growth capital? Or is it a lifestyle brand that supports those who own it?
This question, like all the others on the list is a can of worms. Finding the balance and knowing the timing of when to grow revenue or cut costs is half science and half art/magic.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
Hi, I’m Jayson Koss. I founded Delivery Dudes back in 2009, a simple idea born from a need I saw in my community. What started as a side hustle soon evolved into a massive operation, spanning over 40 cities and making thousands of deliveries each month. It wasn’t just about delivering food; it was about creating a platform that brought happiness, supported local businesses, and offered opportunities to our team.
I believe my real strength lies in building and scaling teams. At Delivery Dudes, I learned that creating a transparent, positive environment was key to our growth. We focused on continuous improvement, always looking for ways to be better, do better, and have fun along the way.
After successfully selling Delivery Dudes, I took some time to reflect and soul-search. This journey led me to found Eightfold Ventures. Here, I’m channeling my experiences and lessons learned into coaching and mentoring emerging e-commerce brands. I’m passionate about helping these founders replicate the success I had with Delivery Dudes, bringing all the tools and insights I gathered to the table.
In addition to leading Eightfold Ventures, I’m also at the helm of Eightfold Labs. My experience with technology at Delivery Dudes has been instrumental here. We’re building Shopify apps and providing tech support to our portfolio companies. It’s all about leveraging technology to empower e-commerce, something I deeply understand and am excited about.
My journey has been about more than just building businesses; it’s been about creating platforms for happiness and growth, both for our customers and our team. Every step has been a learning experience, and I’m looking forward to continuing this journey with Eightfold Ventures and Eightfold Labs.

Let’s talk about resilience next – do you have a story you can share with us?
12 years in the last mile food delivery space, largest regional player, first to profitability, up against SoftBank dollars / Uber / DoorDash.. Survived, didn’t attrit top line, made it to covid tailwind, sold..
Can you tell us the story behind how you met your business partner?
Known him my whole life. Begged him to come work with me once the business was established. My yin to my yang.
Contact Info:
- Website: https://www.eightfoldventures.com/

