The Unexpected Lessons of Starting Over

There's something both terrifying and liberating about starting over.

After our successful exit at Support Shepherd (now Somewhere), many expected me to leverage everything we'd built: our processes, the customer playbooks, our well-oiled machine.

It seemed like the logical next step. After all, isn't that what successful founders do? They replicate their winning formula.

But along the way, I discovered that your biggest strength can become your biggest blind spot.

Life After Exit

Recharged after a much-needed sabbatical, I began to build new businesses following our exit. I invested in a couple of ventures and started building my media production agency, Ember Media.

But as I built these ventures, I realized I was unconsciously trying to force-fit Support Shepherd's late-stage solutions into a day-one startup.

I realized that to succeed in these new businesses, I needed to adopt a beginner mindset. I needed to relearn the art of building from scratch and embrace the messiness of early-stage growth.

Trading Efficiency for Experimentation

Back at Support Shepherd, we optimized for efficiency - something expected from a rapidly growing startup with over 100 employees all over the world. We had processes in place and we hired smart people to make sure that everything ran smoothly.

Now, I'm optimizing for learning and unlearning. Instead of hiring lots of people, I am building with more intention and working with a small but talented team. We’re doing a lot of trial and error. We’re also having a lot of fun in the process.

Experimentation may be intimidating, but it’s a necessary step towards building a sustainable business. It’s also exciting to go back to my roots and retrace how we’ve built Support Shepherd back in the early days.

Instead of following established processes, I'm letting curiosity lead the way. It's uncomfortable, but that discomfort is where growth happens.

My advantage is that this time I am not just starting from scratch — I am starting again with a wealth of experience.

Starting from experience

Speaking of experience, I am grateful to have a bank of lessons from my time at Support Shepherd.

Building that company has taught me a lot of things about myself, how I work, my strengths, and my weaknesses. I’m eager to apply all these learnings to my new journey.

Prioritizing my well-being, for example, is a significant lesson that I’d like to put into practice this time around. Looking back, I realized that I gave too much of myself to work and to others - which led to burnout.

This time, I’d like to prioritize healthy boundaries between me and my work, to set aside time for my loved ones, and to be more present in the everyday.

My new ventures will benefit from the hard-earned lessons of my previous business.

Shifting from operations to marketing

Operations has always been my comfort zone. This time, I’m going out of it to focus on marketing — dipping my toes in content creation and finding my way back to video production.

I've seen the impact of purposeful marketing on a company's growth. Noah Kagan's content, for example, is something I'd like to emulate. Aside from showing valuable and inspiring information in a very accessible way, his video content also serves as a highlight reel for his content company.

Ember Media, my new agency, just produced a series of videos that I hope will pave the way for more inspiring projects in the future. I’m also excited to launch a new podcast called Ignite The Spark, which will feature raw, unfiltered stories from entrepreneurs, artists, and game-changers who built their success by breaking the rules.

Exploring marketing has allowed me to grow in many new ways. My team and I have big plans ahead and I can’t wait to share them soon!

Nurturing relationships

Support Shepherd opened many opportunities to connect with a lot of inspiring entrepreneurs and startup founders. Across time zones and work cultures, the friends I’ve made in my journey have given me a wealth of guidance during — and after — my time as co-founder.

Last but not least, I hope to nurture these relationships and discover new ones as I grow my businesses.

Going Back to Basics

Starting over isn't a step backward. Sometimes, the most powerful thing you can do is give yourself permission to begin again, to question what you know, and to grow in new directions.

My journey continues. And this time, I’m eager to build better, with more intention, more curiosity, and yes, more joy in the process.

How about you? What lessons are you relearning or unlearning?