SJ23 Follow-Up – Advice from Entrepreneurs in the Fray

On our most recent episode, we featured advice from eight inspiring entrepreneurs (and also the Startup Jab team!) at every level of starting and running their businesses. Here is their advice in full:

Bess Winston, managing director of The Winston Agency

I started my own communications agency last year after nearly 20 years working for “big” agencies and the government.

This has been the SCARIEST thing I have EVER done. But if life doesn’t scare you just a little bit, then you’re not doing it right.

What I wish I knew last year? Treat your business (and your brand) like a child. You wouldn’t let any ‘ole body take care of your child. Don’t hand out assignments or work to any ‘ole body. Even if they’re great friends in need of work. The threshold of who gets near your business is simply, do they have the talent to do what you need and can they deliver when you need them to?

My thoughts in general on the most important thing an entrepreneur should do ay anytime of the year is some what cliched, but in my case has been true. If you are REALLY good at what you do, everything will work out. Leap and the net will appear. Be fearless, have faith, and take an Advil when you need to.


Mollie Katz, founder of Mollie Katz Communications

Do things you are a bit afraid to do. Most of them can be conquered if you set aside the fear. When they are, you feel victorious and build strength and additional confidence to take on the challenges of the future.

Be honest about your weaknesses, and actively turn them into strengths. Many of us feel anxiety about what we don’t know or have not done. I find the best way to get past this is to see these as areas where we need to learn more. Convince yourself you want to learn more, and take steps to start learning.

Professional development opportunities aren’t hard to find — they are online, in books, in business media and in the community through networking groups, schools, and business resource groups. Gain the knowledge you need and you will feel empowered and ready to turn your weaknesses into strengths.


Kaitlin Reimann, founder of uBack

It is a marathon, not a sprint! In the first year of a start-up’s lifespan it seems like everything needs to be done “yesterday” and it is tempting to jump on each request immediately. Instead of juggling 100+ activities each day, I would set goals, both personally and professionally, and stick with them.

Set your plan and socialize the plan with mentors, advisers, colleagues, etc. Doing your due diligence and exposing your plan to a diverse audience early-on in the year helps identify strengths and weaknesses in your plan that you may not have otherwise seen until later in the year.


Steve Sunu, public relations manager for Stela

If I could start over again today, the thing I’d bring to the table is I’d want to take a little more risk. We announced in the comics market and it was great and we had a big splash, and there have been a few articles coming out about it since… but I would want to take some more risks in where we hoped to get placement. And where it is we ended up getting placement is great, but it would have been nice to be even a little bit more ambitious then that. Sometimes you gotta start out the gate a little more cautiously; I wish I had known sometimes that it’s ok to swing for the fences a little bit more and take those risks you might normally not want to take if you’re not [at a startup]… It was a really good learning experience and as we go into launch now I’ll be taking a lot more risks and pushing a lot harder.

It’s ok to be scared. It’s what you do with that fear and what you do to help mitigate that that’s really going to drive you moving forward. You have to make sure you’re always working towards trying to alleviate that fear while still being scared – it’s a good thing to drive you forward but work towards alleviating it rather than letting it paralyze you.


Paul and Brittany Mederos, authors of Crafting Your UX Portfolio — A Weekend Guide to Getting It Done

Our sales came in spikes. Spikes are coordinated with marketing. Our biggest spikes were getting on design-centered community sites, for example, and ProductHunt. There was a long-tail effect, but it was pretty tiny. On a spike, we’d get ~20 copies sold, and then it would drip down to ~1 sale per day until the next spike. Interestingly enough, we had a few unexpected spikes, and couldn’t find their sources. We assumed it was private newsletters/in-person meet-ups of some sort, but were never able to confirm by talking to customers.

Once we crossed the 100 customer line, it helped clarify our goals, leading us to the decision to stop selling it (instead, it’s a free guide on Medium.) Our goal was never to build a sustainable product; it was to reach the people who needed it to make a difference in their design careers. The peeps who bought (that we heard from) found it incredibly valuable… in fact, they continue to send us updates on their career months after making progress and getting a job. We decided to open-source it, and post it on the biggest network we could find: Medium.

Our switch to Medium is still early, but super optimistic in reaching original goal. It’s only been a week, but we’ve easily had 10x the traffic with minimal marketing effort. Excited about the much higher reach potential, and the stories (and learning) that’ll come with it.

We learned that a more formal mentorship program might be more useful / higher value. When we sold our book, we had two tiers: $30 for the guide, $100 for guide + 1-on-1 time. We capped the 1-on-1 time to ~5 folks, but we got 10x that number of folks who were willing to pay for the 1-on-1. Because of this, we’ve started contemplating a much higher value course… say a $1,000 1-day course, with periodic check-ins over the course of 3 months. Much more service-oriented, but there’s always a product hidden in a service. 😉

We also learned there’s high demand from the other side: recruiters and companies looking to hire designers. They want to learn what to look for and how to do it well. We’re contemplating putting together a “how to hire a designer” guide for entrepreneurs. Lots more customer development needed, but so far signals are high, and we know it’s MUCH higher value market (e.g. in my own company, I’m looking to hire for my tech team, and I’d pay outrageous amounts for qualified people.)


Mannie T’Chawi, co-founder and CEO of LayerCake

People: It’s vital for you as an entrepreneur to surround yourself with the right people at all times, throughout your journey. Invest in relationships that build your skills, knowledge (both historical and contemporary), network, and passion. Focus your time and energy in positive relationships, always. Not everyone will get you/your vision or support you, so don’t focus on them. Prioritize the people who support you and help you grow in all aspects of your life. They’re the real MVPs!

Read: I’m sure you’ve heard it ad nauseam by now, but read a lot and read often! Keep filling your mind with positive thoughts, skills, and knowledge. Then analyze, contextualize it to your own personality/journey, then apply it. Rinse and repeat.

Places: Most people love to travel, and exotic trips are all the rage; however, what I mean is spend time in places outside your comfort zone. You don’t need to travel to the remote villages of Honduras to understand how other people live. Invest time in making yourself a well-rounded person by going to areas you’re unfamiliar with, unburdening yourself of any preconceived notions, and truly immersing yourself in a culture/lifestyle foreign to your own. Any entrepreneur looking to be successful and make an impact needs to deeply understand the masses they intend to serve/impact.

Share and Share Alike: Tell others not only about yourself and your endeavor, but share with them your journey in earnest: the people who make you great, the literature that makes you smarter, and the places that’ve made you wiser. In doing so you’ll inspire others to do the same, sharing in the wealth of knowledge and resources that they too have at their disposal. There are more than enough opportunities for all of us to win, so share and share alike.


Sarah Meskin and Mal Jones, founders of Rocketkoi

When you’re sick, take a sick day. Your clients will understand and you’re not going to be any use to anybody if you burn the candle at both ends. Actually, your clients will understand most issues that arise as long as you work hard to set up a truly collaborative relationship with over-communication right from the very beginning. Be honest, be open, clients will follow your lead, and be sure to take sick days.


Teague Hopkins, host of Startup Jab and founder of the Teague Hopkins Group

Mine is around the idea of sales, and this is a lesson I’ve learned many times and continue to keep learning. The world is not a meritocracy; we go through our educational experience in a quasi-meritocracy, and then we emerge into the business world and you don’t necessarily do business with the person who’s best at providing the service, right? You do business with the person you like, or the person that’s best at selling it. I had a couple of moments in the past year of seeing somebody sell a project and knowing I could do that project better, but I didn’t sell it. On some level, all right, fine, I didn’t sell it, I don’t need the money, that’s fine. But on another level, the person who’s getting that service is not getting the best possible service. So if you can deliver a service that’s really great, you have a moral responsibility to get good at selling it, because otherwise all of your potential clients are going to miss out on having that really great offering… Part of providing value and part of providing good service is actually being able to sell it.


Jason Nellis, host of Startup Jab and business development for

2015 was a lot more of a challenge for me than I thought it was going to be. As much as I wanted certain things to go the way that I had planned for them, they didn’t, and it was a really challenging year. Being at 2016 now, I’m fortunate to have a company I really love, people around me I really enjoy, and more than anything else a sense of direction. It is not without challenge or bumps…

Be kind to yourself, and be generous with yourself. We oftentimes are our own worst judges, our own worst enemies; things aren’t going to work out the way that we think that they’re going to. You can sign someone to a contract that guarantees you $10,000 a day, and if they can’t pay and it’s unenforceable, then you’re SOL, and you have to be okay with that… It’s easy to beat yourself up. It’s easy to take yourself a little too seriously, to be a little too wrapped up in the details. Have faith in yourself, be good to yourself, and be okay with the fact that things are going to go up and down. It’s not the individual wins or losses, it’s the overall average. If things are trending up, that’s the important thing.


Katie Stanton, producer of Startup Jab and founder of The Good Lemon

When I started The Good Lemon with my co-founder last summer, I had no idea where to start – I just jumped in, absorbing as much information as I could on the fly and talking to everyone I knew who might have something helpful to say. I wish I had known how valuable these relationships would become as my business grew and as I grew as an owner. This is scary and hard and also amazing, and if I didn’t have good people to share the ups and downs with I don’t know where I would be now. It’s not just about referrals or money, although those things are important – it’s about making strong connections with those who genuinely support you, and who you can support in return. (And on the flip side of that, clearing out the relationships that don’t make you feel supported.)

If you don’t do this already, figure out the routine that helps you be the most productive and happy. Having flexibility means being able to do the things you need to take care of yourself – to feel good, clear your head, and feel accomplished – whatever that means for you. For me it’s exercise, travel, and helping friends with passion projects (like StartupJab!). The more you take care of yourself, the more you can give to others; if you don’t take care of yourself, you’re doing a disservice to your business and your relationships.

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