10 Lessons From A Year Of Elevate Labs
On December 17, Elevate Labs hits its (legal) one year anniversary. It’s a bit of a strange date—the date I filed my paperwork, not necessarily when I actually started the company!—but it does mark a great place to stop and reflect on what I’ve learned this past year. Entrepreneurship has been nothing like what I was expecting, and it’s been fun to step back and think about what has been different and what I’ve learned this year.
To give back to all those who helped me in the early days (and still now) by sharing their real stories and reflections, and also to bring some joy and reflection (maybe?) into our lives before the end of the year, I’m sharing here my top 10 lessons from my year of entrepreneurship.
10. The Product Doesn’t Matter
OK, the title of this is a little clickbait-y. But coming out of my corporate job, where the quality of my work was essential, I was expecting the same to be even more true in my own business. After all, the best way to get business is through testimonials, word of mouth, and repeat business!
And while that’s true, I’ve seen over and over that the specifics and details of the products we’re building and selling matter much less than a variety of other factors that influence whether people want to buy what I’m selling.
So what does matter, if the product doesn’t?
My credibility: why should people trust me? I don’t love being the center of attention, so this has been a hard one to swallow. Talking up myself and my accomplishments feels icky. But proving my expertise—and specifically, why my expertise relates to the unique circumstances of each individual client—is critical to getting past the first conversation.
Relationships: I hate this one with a passion, and I have worked so hard this year to prove this false. But ultimately, people are interested in working with people they know, or people that know the people they know. I’ve noticed it’s true for me too—it’s how I hired our initial team, our web designer, our lawyer.
Timing: Is my email about the product arriving right when someone got a call from their boss about how essential this problem is? If not, we can fall under the rug.
Empathy: Every organization and culture is unique, and each has different needs. Entering conversations from a pure state of curiosity and compassion for their situation matters more than explaining how my product fits their needs.
Obviously, the product does matter. And for us to grow according to our ambitions, we need things that are amazing—to drive repeat business, to get positive case studies, and ultimately to feel proud of the work we’re doing. But shifting my focus from making something extraordinary to designing a strategy to package it effectively has been a really hard and identity-challenging endeavor.
Which brings me to…
9. Marketing and Sales: Not the Same Thing
When I decided to start my own business, I knew I was signing up for a lot of sales. Everyone told me that I needed to be great at sales to succeed at business.
What I didn’t realize was that sales wasn’t precisely what I needed to master. Instead, it was marketing:
What is the market looking for right now? Where does my skill set and expertise align with what people are looking for?
Who is my target customer? What motivates them and what problems do they care most about right now?
Where do my target customers hang out, and what is the best way to get in front of them?
How do I explain my product to that customer? And how does that differ based on customer?
How do I create a sense of urgency and necessity for what I’m selling?
I’ll be honest: I am NOT good at this! I feel like I work through these questions anew every few weeks. The best part of marketing that I’ve learned is that you get real feedback quickly, and can make fast adjustments. Every conversation I have helps me build my knowledge to answer these questions better than before.
To share a very basic component of sales & marketing to those of you noobs like me: marketing is getting people into the funnel, and then sales moves people through the funnel. My biggest challenge has been getting people at that top of the funnel stage.
8. My Bed Beats My Office Every Day
The number of days that I got out of bed at 11am is… embarrassing. Without a boss or coworkers waiting on me, it’s really easy to justify and rationalize just staying in bed. Or taking a break to do the laundry. Or making cookies.
Maybe it’s my ADHD making motivation more challenging, maybe I’m just not great at self-motivation… whatever it is, getting myself up and working—or staying focused on working—is really, really hard.
Two things I’ve noticed that get in my way:
I don’t have external goals and milestones: Sure, I know how to project plan, and I’m killer at making KPI spreadsheets and slide decks. But I made them all up. And so that means I can renegotiate and reevaluate them at will. A daily occurrence is my 7:45am mental checklist of what I want to accomplish that day, and my inner demon telling me why those tasks aren’t important.
I’m not getting external motivators: Doing something well lets me check it off my list. But rarely do my tasks lead to an immediate positive reaction. Most of what I do is a step of many to help me incrementally moving forward. I don’t know how or whether most of what I do will directly contribute to our success, everything feels like a shot in the dark.
Sometimes these challenges have shown up as depressive symptoms (ie, not getting out of bed), and other times I’m just more prone to distraction. But more than anything else, entrepreneurship has required me to manifest for myself boss-level motivation.
(I asked ChatGPT to help me rewrite that last sentence, and here are its recommendations that I present without comment:
Entrepreneurship really had me out here manifesting main-character, CEO-era energy just to function.
Running a business basically forced me to unlock boss-mode DLC I did not know I had.
Entrepreneurship said “no mid energy allowed,” so I had to manifest full-send boss vibes daily.
Building a company means manifesting CEO energy even when my soul is running on 3% and vibes alone.
Entrepreneurship required me to self-summon big boss energy like it was a Pokémon move.
7. Timing is Everything
I feel like that old real estate slogan of “location, location, location”.
In all the conversations I have with other entrepreneurs and consultants, I keep coming back to this idea of timing and how critical timing is for success.
I’ve felt the impact of timing in a few places:
Ecosystem timing: The impact of starting a business in 2025 in the DC area is rough. Not only are we in a broad economic downturn, where companies are more likely to be implementing layoffs or spending freezes than investing in leadership and culture, but the DC region has been hit particularly hard. The first sign that my timing was off came in late January and February, when the third of my personal network that worked for USAID or USAID-affiliated contractors and nonprofits were laid off with the dismantling of the international aid agency. But as RIFs have trickled through other government agencies, and the shutdown threatened the future of federally-funded nonprofits, the strength of my network was… not as strong. (I should note here: I feel incredibly lucky to be able to do this at all, and I know so many horror stories of people laid off in terrible situations. Just noting the impact of forces way outside my control!)
Organizational timing: Is an organization ready for what we’re offering, and even more importantly—is it critical for them right now? I’ve known for a long time that leadership and culture feels like the things that’s important but not urgent. If I’m talking to someone when leadership isn’t feeling urgent, it often leads to a, “this is awesome! I’ll come back to you when we’re ready.”
Messaging timing: This one is even more granular: is my message arriving when they’re thinking about it? Many of my wins have come from when I send an email or have a conversation directly after someone realizes they need something.
There have been ups and downs of realizing the importance of timing. It can feel frustrating and like I’m out of control—or the inverse, like it’s not my fault if I’m getting the responses that I want. On the flip side, though, it has helped me get more comfortable going outside my comfort zone: sending follow-ups, scheduling frequent catch-up calls, going to networking events, and generally trying to put myself out there.
6. Leading a Team of Your Own Business: Infinitely Harder Than Everyday Management
I’ve led teams since before the first iPhone release, and I’ve had my share of wins, challenges, and fall-flat-on-my-face fails. But nothing prepared me for managing a team in my own business. All of my challenges with motivation are magnified. Setting direction for a team when I’m getting it from above? No sweat. Setting direction for a team when I’m making it up myself? And when whether my strategy succeeds or fails determines whether they can pay their bills? Different story.
I’m up in the middle of the night many nights stressed about my team and if I can do enough so that they can succeed. I’ve begged and pleaded for work for them. I’ve raved about their strengths to anyone who will listen. I feel on the hook in a way that I never did before.
In our “Executive Compass” services (modified Executive Coaching), we talk about how being an executive—and especially being a CEO—is like living on an island, and I’ve coached many CEOs through this dynamic. Living it myself though has really helped me see how true it is.
5. The Wins Feel Small and the Losses Feel Massive
In August, frustrated by a failure that to be honest I can’t even remember now, I reached out to a friend who started a multimillion dollar biotech company 15 years ago. “I just want an unqualified win,” I told him. His response? “I’ll tell you when it happens.”
It’s really hard to see a win as just a win, and not notice all the downsides or the potential for falling apart. Meanwhile, each loss hits so hard—a combination of a gut-punch to my self-confidence and identity, fears about my financial stability, and worry for my team. It’s made my view of how we’re doing feel really warped. Are we the version I’m presenting on social media, or the one that lives rent free in my head?
So what are some of the wins I’m having such a hard time acknowledging and celebrating?
We built two Leadership Intensives: 9 hours of live, facilitated content with ~4 hours each of asynchronous content
Our Leadership Intensives were really successful! 100% satisfaction with solid gains in leadership skills and fantastic testimonials.
We had participants in the Intensives from 13 different organizations ranging from Big Tech to HVAC repair companies to national nonprofits to the State Department
We ran live sessions on Grounded Leadership, Psychological Safety, Resilience, and Teambuilding to 4 different clients representing nonprofits and companies across the country
We negotiated legit contracts with Fortune 200 companies
We created from scratch a 360 assessment designed to compete with the Hogans and Leadership Circles, complete with integrated AI analysis
We pivoted towards Culture with comprehensive culture services
I wrote a book!!!!!
I’m sure there are a ton of other wins that I miss in the day-to-day challenges of trying to get this off the ground. Reminding myself to acknowledge and celebrate the wins is a daily struggle… but I’m getting there!
4. I Miss My Boss
Not necessarily a specific boss—though I am forever grateful to the great bosses I’ve had, like Shannon Lopez, Grace Chang, Shannon Rinella, Marwa Farooq, Mariyam Farouq, Cheryl Bucci, Ari Katz, Leon Morse… I could go on. But what I really miss is have “a” boss. There are so many days when all I want is someone to tell me what to do, to give me feedback, to set a direction to work towards, to hold me accountable for doing what I said I would do.
Being my own boss is the hardest job I’ve ever had, and trust me—I’m a lousy boss to myself:
I give myself shitty feedback. It’s always “here’s everything you did wrong, now obsess about it for the next 24 hours and think about what it means about you that you got it wrong.”
I use extrinsic motivation instead of tapping into my inner motivation. “Send 10 more Apollo emails and you can have a cookie” is my management tactic.
I prioritize my trees over the forest: I push myself to obsess about the details rather than forcing a step back to reflect on the bigger picture.
I reward busyness—I worked until 5pm, now I can turn off!—rather than results.
I overly focus on others’ success and judge myself accordingly.
I know better than this!! I’m a better boss to others! And yet, when it comes to myself, it’s really hard to implement the practices I would use with others.
3. There Is No Right Answer
One of my recent dilemmas has been around channels for marketing (all of my dilemmas are about marketing). Should I go to that conference, and if so how much money is the right amount to invest in sponsorship? Should I be doing straight cold emails (higher volume) or should I follow the “Show Me You Know Me” system (higher response rate)? Should I pay for a marketing consultant, or should I pay for a mass marketing service?
As I coach executives all the time: there are no right answers. But it’s harder as an entrepreneur. I can get input from others, but I don’t have any guardrails protecting me like I’ve had in previous roles—no manager telling me to do it their way instead or helping me debrief a decision gone wrong. Spending money on the wrong thing? That’s money that’s not going to paying my employees or paying for my kids’ summer camp.
One of the biggest challenges I’ve found with the “no right answer” dilemma is that no one is impartial. I have a massively biased view of what I need to do or what will work—and most of those I ask for advice are either too invested in the results or only see part of the story.
Despite having worked with many nonprofits on board relationships, I never really got the value of a board until now. While we don’t have a formal board yet, I have really been thinking about how to build one and think through the right makeup of expertise and personalities to help me navigate the really hard choices.
2. You Have to Be a Little Bit Crazy
When I first started working with CEOs, I noticed many have a kind of manic energy that seems a little… off? Especially the founders.
Well, I have figured out why it is. As a friend put it, “The people who are successful at this are the ones that keep going when literally every rational person would stop.” You have to ignore all the red flags, push past people telling you it’s time to stop, and do the things that people tell you don’t work (hello, cold emails, nice to meet you!). You have to believe that this thing is possible even when all evidence points to the contrary.
You also need to do other hallmarks of crazy people, like talking to yourself, splurging on things that don’t seem to matter (I will fight you over my way too expensive planner), hallucinating successes, and acting like the dog in the house-on-fire meme.
Entrepreneurship also requires sacrificing things that are honestly non-negotiables. Things like sleep (even when I have the time, the entrepreneur anxieties wake me up!), normal conversations with friends where you DON’T talk about your business the entire time, your pride, your humility, your certainty and stability… all things that seem like I can’t live without them, right?
On a call today, a fellow founder said, “The only reason you would choose this path is if you can’t live without it.” What I’ve learned over the last year is I have so much more to contribute, more ideas and passion to make them a reality, then has ever fit in a job before—even the best jobs I’ve had. The ability to use 100% of my passion and excitement and creativity to make a difference in the world is an incredible privilege… even when it feels impossible.
1. Community is Critical
Which brings me to my final lesson. One of my first calls when I was starting out back in January was with a former coworker who told me that you need community to make entrepreneurship work. As a lifelong extrovert, I knew I was never going to make it if I didn’t have people around me. From old coworkers to area moms groups to former vendors, having people in my corner—whether as cheerleaders, connectors, or honest critics—has been essential for navigating through the high points and the heartache.
The former peer who meets with me once a week to act as an informal advisor
The coworkers who jumped on last minute calls to help me brainstorm
The former vendor partners who helped me refining my messaging and sales strategy
The friends who “test drove” our programs and offerings to make sure we were making something great
The new connections who met for lunch and connected me with potential clients
The colleagues from my USAID days who reshared my posts and helped connect me with relevant organizations
The friends who connected me with incredible thought leaders
The LinkedIn networking connections who turned into true confidants
The parent of my kids’ friends who gave me feedback on my business plan
Everyone who gave me advice, listened to my challenges, engaged with our content, showed up when it felt like everything was falling apart, cheered on my wins, and generally cared about what we’re building.
And most of all, the Elevate Labs team: David, I don’t know that I can form a coherent thought without it first going through the filter of your brain. Thank you for being on this crazy journey with me. Shannon, you are my ride-or-die, and I’m so excited that we’re finally building the company we’ve always dreamed of. Jourdan, you’re the GOAT, working with you is W and lowkey lit. You’re giving sigma vibes, no cap, and that’s not a flex.
I don’t know what the future of Elevate Labs is, despite what my amazing whiteboard vision chart has; none of us can predict the future. But I’m confident that the only way to get there is with community.
Year one down, infinity to go! We’re ready to rock 2026.