Harvest Group recenty reached the 15-year milestone as a company. As I was reflecting on my journey, I found myself thinking of the mistakes made, victories won, and hard-earned lessons along the way. To encourage other entrepreneurs and honor those who have helped me on my journey, I took a minute to write down 15 lessons from 15 years of entrepreneurship.


1. Don’t quit 

As Ben Horowitz highlights in his book, “The Hard Thing About Hard Things”, one essential part of any entrepreneurial journey is having the grit and determination to not quit in the face of daunting setbacks and challenges. I remember having two small kids at home and getting down to the end of my bank account and wondering, Is this going to work out? Nothing worthwhile comes easy – don’t quit when the going gets rough.

2. Anchor to your personal why 

As you go through the challenges of your entrepreneurial journey, others will ask you—and at times, you will ask yourself—why are you doing this? You need to have an answer that is compelling not just to others, but to yourself. My why has been to glorify God with how Harvest serves clients and one another. It has anchored me when I have faced times of trial and uncertainty, from bootstrapping a small business to managing the complexities of a hypergrowth organization. Find your why, and look to it to keep you going.

3. Entrepreneurship is a full contact sport 

In the beginning of my journey, I naively thought that entrepreneurship was all about my mind, but over the years I’ve learned that it engages my mind, my body, my emotions, and my soul. Your ability as an entrepreneur to maintain connectively to your soul, to manage your emotions as you made big decisions, to maintain your physical health/energy are just as important as being an expert and student of your business. Don’t underestimate the impact of starting a business on all aspects of yourself.

4. Don’t get eaten alive 

I wish I had recognized earlier that entrepreneurship can eat you alive. There is always more you need to do, more you could do, more you want to do, more fires to put out, and more people who need your time. Entrepreneurship takes hard work and long hours. I wish I had recognized earlier and been more disciplined in certain seasons of my journey to actively set boundaries to protect time for myself and my family. Entrepreneurship will take every minute you have and keep asking for more.

5. What’s in your wake? 

Like a boat moving through the water, we all leave a wake behind us as we move through life. Sometimes you look at a successful person’s life, and you see bodies in their wake: they’ve used and burned out their people and other stakeholders. Or they’ve kept their knowledge and influence exclusively for their own personal gain. But sometimes you see a leader whose downline is filled with strong, developed leaders whom they’ve invested in and positively impacted. I’ve learned the importance of continuing to say ‘yes’ to people that reach out for help and advice. I’ve found great fulfillment in developing and investing back into leaders, both inside and outside our organization. There is a legacy to leave in the lives of others that is more significant than business accomplishments.

6. Find joy in the journey 

It’s easy when you’re starting a business to stay hyper-focused on where you’re trying to go. However, I have learned that I find more joy in the journey than in arriving at a destination. The mountaintop is a milestone, but it’s ultimately just a moment—we spend most of our time on the journey to that place. The journey of learning and becoming on the way to your goals is one to be savored.

7. Have self-awareness

I wish I had prioritized growing in self-awareness earlier in my journey. Learning the truth about ourselves and facing our flaws is never easy, but ultimately, we can’t grow without it. It took me longer than I wish to learn the value of having people around me that will tell me honestly things about myself that I can’t see.


8. Build a firm foundation 

Early on at Harvest, we received the wise advice to write down and incorporate core values into our culture. Don Soderquist taught me that your values are truly your values when you have stories of how you’ve lived them out in ways that cost you something. We identified our core values and made them the foundation of our company, weaving them into the fabric of our culture and using them to make many cornerstone decisions in our history. Identify the values at the heart of your company and make them the core of how you make decisions and hire, fire, promote, and reward your people.

9. Cut out the cancer 

Sometimes as a leader, cancerous people will make their way into your business, either as employees or as clients. In Harvest’s history, we have had key contributors who were culturally cancerous, and I fell into traps of fear (what will happen to the business?) and justification (but their results are excellent) rather than cut out the cancer early. We have had key clients who didn’t act with integrity or who treated our team disrespectfully, with unreasonable expectations. It was easy to justify keeping them on—they have been with us for so long or what will we do without their business? But in each of these cases, I wish I had acted more swiftly and courageously to remove these influences.

10. Mark milestones & make traditions 

People are forgetful (some of us more than others). Life goes by quickly, with all its good things, hard things, change, and growth, and many of us never pause to appreciate those things because we are constantly focused on what’s coming next. We often fail to pause to memorialize or celebrate meaningful milestones—so we end up forgetting them. Over the years at Harvest we have found many ways to mark milestones, through traditions both planned and spontaneous. Marking milestones along our journey causes us to pause and reflect back, which gives you the perspective you need to press forward in faith and wisdom.


11. Grow talent & business at the same rate 

If you are blessed to experience significant growth as a company, you might find that it is difficult to grow your company’s talent and business at the same rate. At Harvest, one of the keys of our success so far has been our early investment in People & Culture. Over the years, Lindsay Mast, Steve Blair, and their teams have served our mission-critical need to recruit, hire, retain, train, and promote talent at the same pace as our business has grown.  It is easy to make the mistake of only focusing on business growth and neglect people growth.

12. Pivots & Bets 

Don’t get stuck in one way of doing things. I have learned that there are key moments where you need to pivot, changing direction or placing a bet on something new. Being stuck in a certain way of working or remaining too focused on an outdated goal can mean you aren’t ready when it’s necessary for you to take a risk or change directions. Sometimes you recognize these crucial decisions in the moment, but sometimes you can only see them in hindsight. Prepare yourself by being ready to pivot and make bets.

13. You can’t control the speed of the market

One of the many bits of wisdom I’ve received from Steve Graves is, I can’t control the speed of the market. There are times when I want to freeze my kids in a certain life stage and keep them there—the same is true of my company. Sometimes our team, our clients, and our strategy are in a synergetic sweet spot, and I want to freeze them there so that we don’t have to experience more change or “lose” what we have. But the hard reality is, I can’t control the speed of the market. My job as a leader is to lead our team and clients successfully based on the rate of change in the market.

14. Profit vs. people vs. purpose 

At Harvest we aren’t just pursuing profit—we’re also pursuing people and purpose. We feel a healthy tension among all of those. A company that has incredible people and mission but that isn’t financially viable will fail. A company that has a thoughtful, strong purpose and great margin but has the wrong people in the wrong roles will also fail. Any imbalance among the three can pose a threat to your company. But when these three are working in the right balance, they often reinforce and strengthen each other.

15. Thank your heroes  

Along your journey, heroes will come through your company and make a difference that you will find hard to believe. In Harvest’s journey, we have had talented, experienced people come through our doors who were leaving high-profile jobs, and the industry would have told them they should never consider Harvest as a next step in their career. We’ve also seen talented young people contribute above their experience level in roles the industry would have said they weren’t ready for. Time and time again, our people have demonstrated commitment, innovation, and curiosity that allowed them to defy expectations. Harvest Group has been built by heroes that have punched above their weight or that others might say should never have been here at all. I want to tell those Harvest heroes thank you, and I want to encourage you to thank your heroes too.