Business Tips for Entrepreneurs by Kris Rudeegraap

For the final episode of our first season of OctoTalks, we had the pleasure of talking with Sendoso’s founder, Kris Rudeegraap. We invited him to discuss how he is reinventing the way companies boost their lead generation capacities. Here is an extract from that conversation; if you prefer to listen, head to your favorite podcast platform!

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I want to jump right into understanding a little bit more about how Kris sees Kris. I read your Twitter bio, and it says you are passionate about technology, hacker of sales, love the outdoors, founder. So, I see that you wear many hats. How do you define yourself?

I like to think of myself as an entrepreneur, a founder, someone who likes to help other founders. I’m a husband. I have an amazing wife. I love playing golf, I love the outdoors, I’m a traveler, and then I’m a dog dad as well. I think I created that Twitter bio before I got my dog, so I need to update it and add “dog dad” in there. It’s a very important title.

And tell us a little bit more about Sendoso, which I think you consider one of your biggest accomplishments. Tell us all about this business. What is it like?

I founded Sendoso seven years ago as a sending platform for corporate gifts, direct mail, and more. We’ve grown to 300 employees, raised $150 million, gained worldwide customers, and achieved nearly $100 million in revenue. Before that, I spent a decade in software sales, realizing the limitations of email outreach and exploring more effective ways to engage customers, like personalized notes and gifts. This inspired me to create Sendoso, aiming for a streamlined solution to simplify and automate the process.

What I find most admirable about platforms such as Sendoso is that you guys mix software and the physical world, right? You have all the tech components, but then you have to deliver real things to the people’s houses or offices. I bet it’s very challenging, right?

It is. And it’s quite a unique learning curve. Starting about six years ago, our learning curve was unique. Our first warehouse – which was the size of a bedroom – quickly filled up. We expanded to larger spaces, now occupying a massive warehouse, with global presence. Witnessing this physical growth alongside our software development is truly fascinating.

Well, it’s really impressive. You know, Kris, one of our main purposes as a company here at Octobot is to transform people’s lives through technology. And we would love to hear from you. How do you think Sendoso is transforming people’s lives?

So, I think the power of Sendoso was really the power of making people smile. Sendoso’s magic is in the smiles it brings. A gift can spark happiness, and we’ve seen this in countless interactions over five years, like birthday and job-change presents. Creativity matters—a bit of time invested to understand what someone wants or using software recommendations is potent. Picking that perfect gift, with a handwritten note, holds incredible potential. We’ve witnessed all sorts of inventive gestures. One favorite memory involves sending a crutch-bound man recovering from skiing injuries a rack of ribs and a funny note saying “Hey, here’s some extra ribs for you” as a playful touch. These lighthearted, personal approaches stand out in a business world that often over-does professionalism. Amid expectations of seriousness, injecting humor and individuality matters. People connect with people; they like to work with other people. And, you know, once you can kind of bridge that gap and make a prospect or a customer more like a friend, I think that goes a long way and that relationship builds stronger.

Yeah, even though technology advances so much and things are becoming more and more digital, this human touch is still so important and people value it much more; it was a genius idea. Your whole business journey is super interesting, and I would love to know a little bit more about your thoughts on entrepreneurship. What do you like the most about being an entrepreneur? And I also want to ask you if you consider yourself a serial entrepreneur of some kind, or something like that?

Yep, I’m definitely a serial entrepreneur. Starting companies is my jam. Even as a kid, I was the one selling lemonade and mistletoe, hustling and dreaming. College saw me kick off a venture with $25k, a big deal then. I’ve seen startups go from zero to billions. Problem-solving’s my thrill; every day’s an unknown challenge and celebration mix. Customers’ joy is what I dig—seeing them succeed, grow, even get promotions like one who used Sendoso for a campaign and soared career-wise. That gives me goosebumps. Then there’s the team: making dreams real, crafting awesome jobs, and the buzz of creating opportunities—these make entrepreneurship rock.

I love these stories when you can see the real impact. I guess that nowadays, besides all the things you do directly in your companies, you also help a lot of other entrepreneurs, right?

So, I’ve invested in a dozen companies. I’m helping founders in dozens of companies. I like to spend a good portion of my week getting into the weeds, helping founders build their products and get their first customers. I had mentors and advisors when I was in a similar situation as a smaller company, and I’d like to kind of pay it forward and return the favor. I find it very interesting to learn from my successes, learn from my failures, and help transfer those learnings to other entrepreneurs.

And Kris, I’m curious, is there a dream company that you imagine yourself founding and then working there your whole life? Or do you think you are always going to be this guy that has ideas and creates them or helps others create them? How do you see yourself?

It’s a mix of both. Currently, I’m living my dream, but for many companies, there’s a lifecycle. You kick off, get funding, then investors want returns. After a decade, leadership changes or a sale might come up, and it’s a fresh start. Learning spans the journey—from a small startup crafting products and launches to the big league with thousands of employees and huge revenue. Both sides pack unique challenges.

Talking a little bit more about challenges, Kris, what do you think are or have been the biggest challenges that you have to overcome? And how was your process for finding solutions to those challenges?

I could go on for hours here, but I think balancing priorities is a big thing, especially in early company stages. As a founder, you wear all hats—sales, marketing, finance, HR, Product. I got into noting ideas, tasks, and using project management tools. Disconnecting is key too; as a founder you could work 24/7, but life’s more than that. Prioritizing personal stuff matters, like dog walks and dinners. Stop when the day ends; tasks won’t vanish, you’ll get to them tomorrow. This balance is crucial. I shifted from sales to CEO, a hurdle since many founders have tech backgrounds. But my sales angle helped with early customers. Scaling is another beast: nailing product-market fit, gaining paying customers, and building a good sales-marketing dynamic. Then comes hitting the first million, then the ten million revenue mark. It’s tough. Plus, the hiring challenge: assembling a solid team and scaling—both big deals.

Finding the right people sounds like a big challenge to me. Kris, over here I see a lot of examples with Octobot’s founders and how over the years they had to learn how to delegate more and start focusing on what matters and in finding the right people that could do things and lead things that they couldn’t anymore. What are your thoughts on that? How have you found the right partners or the right people to complement you?

I think being a good delegator is one of the key strengths of a founder and a CEO. There’s loads of things to tackle, doing it all means doing nothing well. Focus on areas you’re passionate about. You can’t ace everything, so delegation’s key; and delegating means trusting, and not micromanaging later. As a leader I try to motivate, celebrate wins, and provide feedback that fuels growth. In team management, it’s vital to let your people shine—I often tell my Sendoso crew that I work for them; they’re the CEOs of their domains, and I’m there to clear paths, find resources, and make them their best. Letting smarter folks work unfettered is vital.

That’s a great thought. I wanted to talk more about team management and leadership in general, Kris. What have been your lessons besides this one you already shared? Do you have inspiring leaders or leadership styles that you aspire to?

Positivity is my lead style, I think encouragement is important. While fear-based leadership works for some, I prefer the smiles and constructive feedback route. Even when someone makes a mistake, a positive approach and constructive feedback will spark better solutions and harder work from them. Learning’s ongoing: you have to join leadership groups, observe your peers, and read a lot. Setting an example is vital, too. I like diving into the trenches with the team, helping solve issues, even hopping on calls with customers. I like being hands-on, not distant in a big office thinking I’m too cool for this work.

Does it ever happen that you join your team members in a call or a meeting and they feel a little bit intimidated, like, “Oh my god. The CEO is here”?

I think for some new employees that maybe don’t know my style, which is getting involved, they’re like, “Why is the CEO on this call?” or “Why did the CEO Slack me?” But as people get to know me, it becomes something they love, because they can Slack me any time and say, “Hey, I got this idea”, or “Hey, what do you think about this?” and I’m quick to respond and to follow up. I think it does need a little bit of getting used to, given that some other CEOs maybe are way more far removed, but I think people love it once they get used to it.

Yeah, I think it’s a very good leadership style. Kris, you mentioned before when we were talking about challenges that you come from a sales background and you said it was a bit of an adjustment for you, right? Moving from sales to being a CEO. Tell us a little bit more about that. What are the pros that your background brings and what things are more difficult?

My sales experience toughened me up to handle customer rejections without getting hurt. Sales teaches you to bounce back from nos, which is crucial in the early startup grind. Facing skepticism or no-responses is part of the road. Talking to customers upfront, diving into sales intricacies early, it helped me. Then comes hiring, which is like selling the company to candidates, and convincing them to jump ships for the unknown potential of a new company. It’s salesy, and I embraced that. Raising venture capital is another arena where sales skills shine. Pitches, demos, follow-ups—it’s all about selling your idea to VCs. You face many nos, but those yeses are worth it. On the flip side, not having much experience in product engineering was tough, and I learnt a lot during the early days, when you need strong product management, customer insights, and engineering chops.

Nice. Well, as we are talking a little bit about your past and background, I also wanted to ask you if you could go back in time, Kris, and do something differently, would you do that? Or is there anything you would like to say to Kris from a few years back?

Honestly, probably not. I love where I’m at; what I’m doing is exactly where I want to be. Maybe I’d buy some Bitcoin when it was like 10 bucks or something. But besides that, I think I’d do exactly the same. I was doing what I thought I should do 10, and 20 years ago, which is taking chances, taking opportunities, learning from mistakes, and taking risks.

I love that, Kris. And I feel like this episode is going to be super inspiring for other people out there that want to build a product, that want to build a company. If you had to give a few more tips to those potential founders out there, what would you tell them? What is your gold advice to entrepreneurs?

If you’re debating, “Should I do it?”—do it now. No need to quit your job; kick off with a side project. Break your comfort zone, learn, network. Partnering up is great; having a co-founder can be a huge benefit. Attend networking meetups, connect with people. If you’ve started, talk to a customer today. It’s never too soon; you don’t even need a product. Ask about their struggles, show them sketch ideas, share concepts. Act today. Make your move today.

I love the message. You know, Kris, one of the topics that has appeared during these conversations we are having with OctoTalks is this huge transformation moment that we are living with AI and all of these new technologies. There are opportunities there for sure, and also there is a lot of fear of where we are heading, right? I would love to hear your thoughts on this topic. Do you have an opinion about this? Is there something you are already trying with AI that you find interesting?

Yeah, I think AI is going to be transformational for the next couple of decades. I think there’s going to be a lot of disruption to old industries. I think there’s going to be a lot of really cool new technology, and I think it’s going to really complement a lot of existing products or existing human-led processes where AI can make things easier, and can make a person feel like a superhuman by doing twice as much work. In some industries it might replace some people, but for the most part, it’s going to complement and make people much more effective and successful. It’ll be interesting, I think we’ll see a lot of winners and we’ll see a bunch of losers coming out of this in the next decade. But it’s a great time to be alive. It’s a great time to start a company. And AI is one of the most interesting revolutionary changes that we’ve seen in the past 20, 30 years.

Well, and talking about the future, what can you tell us about your future, Kris? Do you have any plans for new businesses, are you working on something new?

Yeah, I’m always working on new things. I’m always trying to help other founders, and always looking at the latest and greatest technology to invest in.

Having Kris as a guest was entertaining and left us thinking a lot about new ideas. We loved his creativity in solving problems with his platform – if you’d like to listen as well, the full episode is available here.