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Strategy
Just DON'T Do It: Five Reasons NOT to become an entrepreneur
By
Mike Smerklo
on
October 16, 2020
August 29, 2022
Entrepreneurship is nothing if not a challenge. Ask us, and it’s truly the ultimate challenge, one that requires unparalleled levels of strength, creativity, flexibility and conviction – often all at the same time, multiple times a day for years on end. Contrary to what many sources of entrepreneurial advice will tell you, there is no formula to success. You can try to reverse engineer another founder’s playbook or execute another company’s road map, but the reality is that your company’s trajectory is unique.
That’s a huge part of why we’re devoted to providing Next Coast Ventures portfolio founders with one-on-one support, guidance and resources through our firm’s platform function. As a firm made up of former entrepreneurs and operators, we know how crucial it is to have a source to tap for help. In fact, it can be everything when you’re building a company from the ground up.
With that in mind, we created this guide for all founders looking for insight, answers, wisdom and new ideas as they grow and scale. It includes some of our most-read articles over the years to provide you with a well-rounded view on our best advice.
Board Management Advice for Entrepreneurs: As the CEO of your company, you’re steeped in all kinds of information about your company that your board may not be up-to-date on. Here’s how to get the most out of your next board meeting.
Board Management Wisdom from Silicon Valley Legends: What Mike Smerklo learned from Bruce Dunlevie, Bill Campbell, Marc Andreessen and Al Davis about creating, building and managing a world-class board of directors.
When Board Meetings Don’t Go Perfectly: If your most recent board meeting left you feeling less than perfect, here are reasons you may actually be doing things exactly right.
Time Management for CEOs: How will you use your most precious resource wisely as you build your company? Read on for time management lessons learned from Mike Smerklo’s time at the helm.
A Simple Matrix for Solving Time Management Struggles: Use this 2X2 matrix strategy for quick improvements to your time management challenges.
How to Make Decisions as an Entrepreneur (part 1, part 2, part 3): With hundreds – if not thousands – of decisions cropping up every day, founders need a strategy to cut through the noise and make choices quickly.
Avoid These Common Career-Sabotaging Pitfalls: Want a long, healthy and productive career? Here are five things to avoid at all costs.
Think Like a Venture Capitalist: Dig into this post for seven steps entrepreneurs can take to significantly increase their chances of raising capital.
Choosing a Great Capital Partner: All investment is not created equal. Strategies for finding and landing the venture capital relationships that are right for you.
Investors are from Mars, Entrepreneurs are from Venus: Before you can fundraise, you need to understand who you’re talking to. Read on for insights into the minds – and priorities – of the people on the other side of the table.
Founder Insights: The Power of an Executive Coach: Five things to know about executive coaching as a startup founder.
Mentorship And The Monster Under The Bed: Five lessons on how mentors can help you keep moving forward on your entrepreneurial journey.
To Avoid An Entrepreneur's Biggest Dealbreaker, Find A Mentor: Why finding a mentor is crucial to entrepreneurial success.
Being Done and Being Okay With It: Done right, entrepreneurs can feel good both about being done with a current startup or role and how the decision was made.
Why Entrepreneurs Shouldn’t Be Afraid to Ask for Help: It’s not easy to persist through unprecedented leadership challenges (without losing your mind in the process). The key? Asking for help.
Steps to Hiring a Successful Sales Leader: It’s time for you, dear founder, to hire a sales leader and step aside. Here’s how to do it right.
5 Things Every Company Must Do Right Now for Customer Retention: Actionable strategies drawn directly from our Portfolio-only event featuring Gainsight CEO Nck Mehta in conversation with Next Coast Ventures Co-Founder and Managing Partner, Mike Smerklo.
Who Should Customer Success Report To? Here’s an argument for setting up your org chart so Customer Success reports directly to the CEO.
Entrepreneurship and the False Positives of Early Sales: How to think about your company’s first big sales win and what it means for your future performance.
Is Your Brand Hard to Find Online? Tips for up-leveling your marketing with quick, simple steps.
The Role of Transparency in Building a Brand: How one Next Coast Ventures portfolio company leveraged transparency to create a trusted brand.
The Dos and Dont’s of Working with the Media: All press is good press…or is it? Important things to keep in mind for startups considering their next PR push.
Recently, Next Coast Ventures discussed the power of an executive coach with Julia Cheek, CEO and Founder of Everly Health, and Mike Smerklo, Next Coast Ventures Co-Founder & Managing Director. This blog post summarizes the discussion and offers best practices for working with an executive coach as a startup founder.
We all know the myriad of challenges start-up executives face – and Julia and Mike have not been exempt from this. Early in her entrepreneurial journey, Julia hired an executive coach and continues to use one today as Everly Health has grown into a multi-brand, multi-billion-dollar business. Mike is a strong believer in executive coaching, as he has used one himself as an entrepreneur and often sees some top entrepreneurs using them. Research from PwC and the Association Resource Center1 concluded that the average ROI for companies investing in executive coaching was seven times the initial investment – a statistic that’s hard to ignore.
There were five key points that came up throughout their discussion, which we will dig into, covering best practices when working with an executive coach as a startup founder.
A diligently thorough process of getting to know each other to discover the best-matched coach for your personality and your professional journey is required when finding an executive coach. Nowadays, there are platforms that help to facilitate finding a coach, but Julia recommends asking fellow founders and board members for their executive coach recommendations.
Meet with your coach a few times to ensure you work well together. Julia recalls that when she first met Christina (name changed for privacy), Christina made it clear that it was important for them to get to know each other first before they committed to a coaching relationship. She wanted to ensure that the relationship would be the right fit for both of them and ultimately bring high value.
Being a solo founder has a lot of benefits, but it will also leave you facing a lot of struggles alone. Julia recognized this early on and said that she was honest with herself about being a first-time founder and knew she needed support along her journey. Alongside coaching, she needed a sounding board and someone to help provide entrepreneurial guidance (a role that is oftentimes filled by having a co-founder). Julia was lucky to have found her executive coach, Christina, who has been a successful operator in the past and understands the entrepreneurial journey.
The reality is that it can be difficult to be a solo founder. Leveraging an executive coach is a great way to overcome that by gaining the support you are missing from having co-founders.
Julia leverages Christina in helping her gather feedback, reflect on it, and implement new strategies going forward. Additionally, on an annual basis, Julia and Christina work together to gather 360-degree feedback from Julia’s executive team and board members. Christina and Julia work together on the feedback to prioritize the three key things that will make the biggest impact to both the business and Julia’s leadership abilities.
Julia shares the feedback and her key initiatives with her leadership team. This fosters a culture that is both receptive to feedback and encourages personal growth, which is one of the things that impressed Mike most about Everly Health early on. Mike has worked with dozens of executives during his time at Next Coast and is a big supporter of 360-degree feedback for every founder and executive.
There are two important points to keep in mind when evaluating executive coaches. One, your executive coach doesn’t necessarily need a founder background or specific-industry experience, and two, you may not have the same coach throughout your entrepreneurial journey. It’s up to you to decide what characteristics are important to you in a coach and when.
Just like in any relationship, it’s normal that you can outgrow each other. Realizing that this can happen will save you from wasting your time in a dynamic that no longer brings value to you.
Mike and Julia both stress that no matter how busy you are, make time for your executive coaching session. It’s a bit like therapy. When you are deep in the trenches and very stressed, that is when you will benefit most from your coaching sessions. Your coach can help you work your way through and gain perspective. It may feel like the last thing you want to do, but Mike and Julia both expressed their gratitude for having coaching sessions during those moments. Don’t postpone your sessions.
It should be self-explanatory, but it’s a good reminder: you get value from your coaching sessions only if you are willing to put in the work. You need to be in the right mental framework, so recognize that getting into that headspace may be half the battle. Prepare adequately when needed, stay open-minded, and commit. You will see growth.
Note: Coaching should not be seen as a replacement to therapy. There are different resources to support founder mental health.
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Speaking with Julia and Mike, you can see their passion for the subject and how big of a role it has played in shaping them as executives throughout their careers. No matter how early or far along you are in your career, hiring a coach can be game changing.
We hope that these best practices have given you perspective for your own executive coaching journey as a founder. Follow us on social media (LinkedIn and Twitter) and sign up for our newsletter to stay updated with our latest content.
ABOUT JULIA CHEEK
Julia Cheek is the Founder and CEO of Everly Health, the digital health company at the forefront of the virtual diagnostics-driven care industry. Julia founded Everlywell, the consumer brand of Everly Health, in 2015 to provide consumers access to affordable at-home lab tests that include insightful, easy-to-understand results. Everly Health and its consumer and enterprise brands have served tens of millions of people and support dozens of major health plans to close gaps in care.
ABOUT MIKE SMERKLO
Mike Smerklo is an experienced entrepreneur, investor and business leader driven by the desire to turn ideas into reality. Having bought and scaled a small business into a publicly traded company worth nearly a billion dollars in value, he has a deep understanding of the hard work, dedication and grit that truly powers successful entrepreneurship. Today, as the co-founder and managing director of Next Coast Ventures, Smerklo is a champion for a new generation of entrepreneurs building disruptive companies in big markets.
SOURCES
1. “Coaching: It’s Not Just for Executives Anymore”, SHRM, April 30 2021. Author: Andrew Deichler. Access:
At Next Coast Ventures, we are built by entrepreneurs for entrepreneurs. We continue to focus on improving the way we support our founders in their entrepreneurial journey. We heard from our portfolio that beyond day-to-day oversight, a key way to provide support is by engaging the best experts to talk about specific topics. So we are pleased to share the takeaways from our first speaker event of the summer “Customer Success: Retaining Your Customer Base in Challenging Times” with Mike Smerklo and Nick Mehta.
Our Head of Platform, Kaitlyn DeBernardo, is constantly engaging with both our portfolio companies and our expert network to surface high-impact, relevant, content. This event was invite-only to our portfolio but the insights were so strong that we wanted to share them with the entire entrepreneur community.
We think Mike and Nick were the perfect pair to double-click on the topic. Prior to co-founding Next Coast Ventures, Mike was the CEO of ServiceSource, a leading provider of outsourced inside sales, customer success, and renewals management solutions for enterprises worldwide. Nick is the CEO of Gainsight, which provides companies with insights on scalable, durable growth through product-led, customer-led, and community-led strategies. So Mike and Nick are the OGs of Customer Success (maybe more the “O” than the “G”, but still pretty smart on the topic). With the tech market pull-back and the talk of a possible recession, now seemed like the perfect time to have this discussion - and Nick exceeded expectations!
Takeaways:
Fun fact: in 2013 Nick recalls customer success manager roles numbering around one thousand. Today that number has grown to over 300K. What’s more, a company’s customer success is a core topic among its C-suite, at its board meetings and with leading early and late stage investors.
“The move to SaaS and cloud shifted all the power into the customer's hands. [Customer success] went from something that was important to something that was just existential. And now, 100 percent of tech companies have customer success teams,” says Nick.
Without customer success baked into the recipe, Nick says, “especially for early stage companies, you think it's a sale. [Customers] think it's a pilot. That's the bottom line.”
This reality is fueling an industry trend among early stage startups towards hiring customer success team members early – even before sales. That way, companies have the chance to integrate customer success into the user experience from the beginning. While you can fix a sales problem, it’s far more difficult to course-correct a fundamental disconnect between your product and your users’ perception of the value it’s bringing.
A great example is working well at Gainsight, where the customer success team hosts regular office hours, something companies can easily do to engage customers and increase retention. The set up can be simple:
Other options for scaling customer success without hiring include building product walkthroughs, online communities for your customers or automated guided tours.
Nick’s recommendation is D.E.A.R, which stands for deployment, engagement, adoption and ROI. Let’s break that down:
🎧 Listen to Nick talk about D.E.A.R. and why it works 🎧
Along with that, Nick says SaaS companies need to think broadly about product, sales, and customer success together as equal drivers of success vs. operating from independent silos. On a practical level, this can look like customer success managers meeting monthly to determine common themes they’re finding in their interactions with customers, then working to uncover why those themes are present. From there, it is much easier to relay the takeaways from customer success to sales and product teams effectively. On that note, automation can come back into play using tools like recording software to share snippets of customer’s feedback directly with relevant teams. “There's no substitute to hearing it in the customer's own voice,” says Nick.
Want insights from our team and future events like these? We’re planning them for portfolio founders all the time. The best way to get to know us better and follow along: start by subscribing to ATXnology, our quarterly newsletter focused on the pulse of Austin’s startup scene. We’re excited to continue bringing you insightful content from the resources we’re continuously building for founders. If you know an amazing founder who you think needs to know about our approach, send them our way. We’ll be here.
Many thanks to Nick Mehta and the Gainsight team for your participation in this recent portfolio event.