Kelly Bub Smith of Dotted Lines: Five Things I Wish Someone Told Me When I First Launched My Business or Startup

An Interview With Doug Noll

You can’t be afraid of failure… you’re going to fail lots of times along the way but grit and perseverance through the challenging times are what will separate you from the rest.

Taking the risk to start a company is a feat few are fully equipped for. Any business owner knows that the first few years in business are anything but glamorous. Building a successful business takes time, lessons learned, and most importantly, enormous growth as a business owner. What works and what doesn’t when one starts a new business? What are the valuable lessons learned from the “University of Adversity”? As part of this interview series, I had the pleasure of interviewing Kelly Bub Smith.

Kelly is a business lawyer and a strategic business partner who understands the real-life challenges that business owners face, which is why she co-created Dotted Lines Co., LLC, a company that brings professional, trustworthy, and cost-efficient legal education and contract templates to entrepreneurs to help them achieve their highest level of success possible. Kelly is an accomplished lawyer with over a decade of legal experience and a mother of 2 young children. Graduating as Salutatorian of her law school class, Kelly has worked for a prestigious international law firm as well as General Counsel for a successful serial entrepreneur before joining Kristin Santamaria in the formation of Dotted Lines.

Thank you so much for joining us in this interview series! Can you tell us a story about what brought you to this specific career path?

I’d always been a great student, so law school seemed like a natural path for me coming out of my undergraduate degree. I started my career at a prestigious big firm which was an incredible experience and an opportunity for me to be exposed to many sophisticated legal issues in a short period of time. However, since I was a young girl, I had always had a very entrepreneurial heart, so law firm life felt like something was “missing” for me. I left the law firm to work for a collection of entrepreneurial companies, which was an incredible fit and gave me the opportunity to learn the way things worked in the “real world.” However, I still very much desired to have ownership over my own company at some point in the future.

My business partner, Kristin, came to me after she started her own nutrition practice, and she realized there was a gap in trustworthy and accessible legal resources for start-up practitioners like herself. She thought I would be a natural fit to partner with her to form and grow Dotted Lines given my entrepreneurial background. When she came to me with the idea for what would become Dotted Lines, I immediately latched onto her vision and knew that we could go on to create a legal information and contract powerhouse with our complimentary skillsets.

Can you tell us a story about the hard times that you faced when you first started your journey?

When Kristin and I first started Dotted Lines, I was incredibly overwhelmed by the technical sides of launching a business — from the website creation and development to the different integrations we needed to find a way to deliver a smooth sales process to our end customers. Kristin and I became frustrated when we realized that we could not find one software with all the functionalities that we needed, so it felt like it took a lot of extra time, care, attention, and money to get our platform built to give our customers the complete first-class buying experience that we desired. I learned that perseverance is key, and Kristin has much more patience than me… so, I must credit her with being a great partner and helping me remain patient as we worked through the issues to get to the ultimate customer experience that we desired.

The other difficult part of getting started was the patience that it took to grow our audience. I had this very unreasonable expectation that we were going to make our first Instagram post announcing our business, that it would go viral, and we would have a massive following overnight. Realistic, right? I’ve learned that a successful business doesn’t happen instantaneously, and I’ve gotten comfortable with the fact that it’s going to take hard work to get our name out there to the right audience and build a following. Slow and steady really does win the race… it’s so rewarding as we get our name out there and get recognized by other entrepreneurs. Their positive feedback of how much we have been able to help them and their business through our offerings has been so fulfilling.

Where did you get the drive to continue even though things were so hard?

I have so much passion for our mission, which is to deliver trustworthy and professional legal contracts and legal education to entrepreneurs in a way that is accessible and cost efficient. I have seen firsthand how entrepreneurs can change both their own lives as well as the lives of their families and communities through owning their own business, and I have also seen the ways things can go wrong for people who don’t get proper legal protection. I consider myself very fortunate to have a legal education, and I know there are many people in the world without a legal background who simply don’t realize all the risk that is lurking out.

The good news is that all that risk doesn’t have to be scary! It can be greatly reduced if managed properly. It’s incredible that you can protect your whole livelihood with proper legal protection, and I want to continue to encourage and support entrepreneurs in their journey by giving them the resources they need to protect themselves. I’ve also learned that entrepreneurs who feel they are adequately protected are much more likely to feel comfortable growing their business with confidence. There is no better feeling than knowing I had a part in the growth story of an entrepreneur’s business, and this is really what keeps me going.

So, how are things going today? How did grit and resilience lead to your eventual success?

We are making incredible positive momentum and strides. We only launched about 6 months ago, and we’ve already built out several affiliate collaborations with prominent and well-respected leaders in the space and we’ve been invited to present educational modules to prestigious organizations in the industries that we serve (originally health, wellness, and nutrition professionals but have recently expanded to business coaches too). We’ve also built out a strong e-mail list and customer base, and we are working on increasing our social media followings.

Grit and resilience have been key. We’ve heard our share of “no’s” along the way, and the key has been not letting one or two “no’s” stop us from continuing to make progress with everyone who tells us “yes”. We strive to make Dotted Lines better every day.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

One of my funniest mistakes was probably my first few reels. It was so intimidating to put myself on camera, but I knew I had to just do it! It has gotten easier with time. I think a lesson I have learned from that is to not take myself too seriously… I received a lot of feedback from family and friends about my reels. They told me they were too long… I was too close to the camera… I should have chosen a different filter… etc. I know this feedback all came from a good place, but it was still hard to hear! I felt so vulnerable putting myself out there on reels, and my closest family and friends were essentially telling me they were no good! At the end of the day, it has really helped me to be more receptive to feedback and realize that it’s okay to have weaknesses — and apparently one of mine is recording reels! I think that adopting a humble mindset and being receptive to constructive feedback is essential as an entrepreneur — even if it’s hard to hear.

What do you think makes your company stand out? Can you share a story?

There is so much that stands out to me which makes Dotted Lines unique. First, Dotted Lines makes getting legal education and contract templates accessible in a world where most legal costs are exorbitantly expensive and out of reach for start-up entrepreneurs. The truth is… the legal model is still a bit of a dinosaur, and so much of the legal world still operates with lawyers in suits in big downtown buildings charging $1,000 plus per hour. The model is broken and does not serve our communities like it should since many people who need legal help either do not know where to find it or can’t afford the hourly rates charged.

Contract templates allow a venue to provide much more cost-efficient access to entrepreneurs, and I would say that Dotted Lines has distinguishing features even within the contract template space. First, in addition to providing templates, Dotted Lines also includes tutorial videos on how to complete the templates and explain the provisions of each contract with every purchase. Second, our Legally Ready bundle program includes educational lessons on over 40+ legal issues you may encounter as an entrepreneur on a day-to-day basis (think “how to terminate a bad client relationship” to “how to protect my content” to “how do I define my refund policy” to name a few). Further, our templates were developed for specific niches… primarily entrepreneurs in the health and wellness space as well as business and mindset coaches. Many contract templates that you can find out there were not developed specific to the niches we serve, so they do not understand or address the unique pain points of the entrepreneurs we work with. Plus, my co-founder has her own wellness practice, so we were able to draw from lessons learned within her own practice and respond to those more specifically in our offerings for health and wellness practitioners.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

A couple tips… the first is take care of yourself! It’s easy to get overwhelmed with all the “to do’s”, but I have a few non-negotiables that I always must complete first before I dig into any Dotted Lines tasks. First, I prioritize strength training at least 3 times per week, and I always start my day with an organic green protein smoothly. I’ve realized that by taking care of myself, I have so much more energy to keep showing up for my business and not burn out.

Second, do not be afraid to outsource the areas where you don’t have expertise. In our case, Kristin and I are phenomenal lawyers — that is our specialty! But, we’re not great at web design, have no marketing background, and have no experience writing copy. Rather than trying to “google” yourself to death building skill sets outside of your expertise, we’ve found it works so much better to simply hire the right experts in these areas and trust your team. Even with that help, there’s never a shortage of things to do and usually the pros can do it much better than you could!

In a way, that’s also why we created Dotted Lines. The idea is that we can be an outsourced stop for all things legal information and contract templates for entrepreneurs.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I’d have to say my mom. She worked tirelessly when raising my brother and myself, and she taught me to always go the extra mile on everything I do. I know that without her support and encouragement, and frankly, her setting very high expectations for me that I would not have achieved everything I’ve done today.

I remember being in grade school and having projects getting assigned to me. I’d probably do a “B+” job on it on my own, but she always went out of her way to show me how to take things to the next level and make sure to get the “A+”. I remember one evening in particular… she took me out at 9 o’clock at night to the arts & crafts store to make sure I had all the supplies I needed to finish a project to the best of my ability and not just be “good enough”. Now, when I get tired or want to give up, I think about this work ethic that she taught me. It’s been critical as an entrepreneur where we have no shortages of tasks and being a self-starter is vital.

How have you used your success to bring goodness to the world?

I really believe that Dotted Lines legal templates and education is bringing goodness to the world everyday by allowing entrepreneurs to have the confidence they need to grow their businesses and protect their livelihoods. The work of the entrepreneurs we help is crucial. First, it allows entrepreneurs to live their own fulfilling lives, but their work has a ripple effect of then benefitting the lives of so many others. They not only benefit the lives of the contractors and employees they hire, but they also benefit the lives of the customers and clients that they serve. Many of our customers are in the health, wellness, and nutrition space, and it is incredible seeing the way that these health and wellness professionals are changing the lives of their clients every day for the better.

What are your “5 things I wish someone told me when I first launched my business,” and why? Please share a story or example for each.

1 . You can’t be afraid of failure… you’re going to fail lots of times along the way but grit and perseverance through the challenging times are what will separate you from the rest.

We’ve had plenty of tough days in our business… I recall one day where we did an incredible presentation for a target audience, and we had no sales come through that day. I was so disappointed after all the hard work we had put into the presentation. It would have been easy to just call it quits… but we kept going and the sales started to roll in. And even better, we started getting incredible feedback from the customers who purchased. I realized that had we called it quits after that first presentation, we would not have been able to show up and help the many, many customers that ended up later finding us.

2 . Be open to outsourcing — bringing in the experts will not only save you time, but it will make you better.

Kristin and I have outsourced help on everything from business mentorship to copy writing to web design to social media management to public relations management. We have been blown away by the work of our service providers, and we have always walked away so glad that we brought in the experts to help us with aspects of our business where we did not have expertise.

3 . Don’t take yourself too seriously. It’s okay to let your authentic self shine through in your business, and people will be able to sense if you are being authentic or not.

One of my favorite parts of owning Dotted Lines is the chance to show up authentically every day and put on our flair on every aspect of our business.

4 . Find a business mentor if you can. Learn from them.

Kristin and I have had both paid and unpaid business mentors along the way. We’ve learned so much from them. Don’t be afraid to ask questions… and make sure to pay it forward to those who could use your mentorship in the future!

5 . Have an abundance mindset.

It’s easy to get caught up in what your competitors are up to and to let these fears hold you back. I always think of the world as a pie that can get bigger. There’s plenty of room for all of us, so don’t let fear of other competitors in the space keep you from jumping in.

Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

I’d say make sure you stop to celebrate your wins along the way. It’s so important to avoid burnout and keep going.

The lows can be tough… for me, it usually helps to take a break for a bit. I go back to the fundamentals of exercise and taking care of myself. If those things are in order, I can handle the lows so much better. And then, I think it goes back to not taking yourself too seriously. I don’t think I laugh harder in the world with anyone than Kristin — which is just one of the reasons she makes an incredible business partner for me in Dotted Lines. I think laughter can be such good medicine… if things don’t go as well as we hoped, sometimes the solution for me is to make light of what went wrong and just have a good laugh with Kristin about it. We never mind making fun of ourselves. Then, we pick ourselves back up and figure out how to do it better next time.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

This is a great question. I go back to our mission of serving entrepreneurs. I have seen firsthand how positively entrepreneurialism impacts our world… look at the amazing inventions and services that have come out of entrepreneurs from our society over time, and not to mention the jobs and ways that these entrepreneurs ultimately positively affect our whole economy. It truly has a ripple effect. So, my answer would be to support these entrepreneurs and to not let concerns of legal woes or lack of understanding of the legal system be holding any entrepreneur back from either getting started or intentionally staying small out of fear of liability that comes with the growth. These entrepreneurs are changing the world, and the opportunity to help them protect and grow their business with confidence is so rewarding.

How can our readers further follow your work online?

Find us online at www.dottedlinesco.com or on Instagram @dottedlinescontracts. For any entrepreneurs out there, we’d encourage you to check out our free guide which has our Top 15 Steps to Get Your Business Legally Ready. It can be downloaded for free through our website.

This was very inspiring. Thank you so much for joining us!

About the Interviewer: Douglas E. Noll, JD, MA was born nearly blind, crippled with club feet, partially deaf, and left-handed. He overcame all of these obstacles to become a successful civil trial lawyer. In 2000, he abandoned his law practice to become a peacemaker. His calling is to serve humanity, and he executes his calling at many levels. He is an award-winning author, teacher, and trainer. He is a highly experienced mediator. Doug’s work carries him from international work to helping people resolve deep interpersonal and ideological conflicts. Doug teaches his innovative de-escalation skill that calms any angry person in 90 seconds or less. With Laurel Kaufer, Doug founded Prison of Peace in 2009. The Prison of Peace project trains life and long terms incarcerated people to be powerful peacemakers and mediators. He has been deeply moved by inmates who have learned and applied deep, empathic listening skills, leadership skills, and problem-solving skills to reduce violence in their prison communities. Their dedication to learning, improving, and serving their communities motivates him to expand the principles of Prison of Peace so that every human wanting to learn the skills of peace may do so. Doug’s awards include California Lawyer Magazine Lawyer of the Year, Best Lawyers in America Lawyer of the Year, Purpose Prize Fellow, International Academy of Mediators Syd Leezak Award of Excellence, National Academy of Distinguished Neutrals Neutral of the Year. His four books have won a number of awards and commendations. Doug’s podcast, Listen With Leaders, is now accepting guests. Click on this link to learn more and apply.