5 Common Questions I Get About Bootstrapping a Business

5 Common Questions I Get About Bootstrapping a Business

This month marks two years since I launched First Peak! And as with any birthday or anniversary, the arrival of this two-year milestone brings forth all sorts of reflections and emotions. I’ll spare you the full brain dump that landed in my journal, and instead focus here on some of the most common questions I get from other entrepreneurs – mostly women, many mothers – who are considering bootstrapping their own small businesses. 

My hope in writing down these answers is in part selfish: to process and preserve this journey as a transformative segment of my own professional career. But my hope is also that sharing my experience can nudge others onto entrepreneurial paths, or serve as a prompt to consider what it may look like to listen to that creative itch.

How did you get over the hump from having an idea to actually building a business?

There were about 9 months between the day I thought of First Peak and when I started selling products. This is by some estimates a relatively “fast” turnaround, but for me, it was simply an exercise in trying to build and then follow momentum. There were a few steps that really helped me along:

  1. Once you have the idea, talk about it! There’s something inherently scary about sharing a new idea with others, but with that vulnerability also comes accountability (others who will ask you how it’s going) and often help (suggestions, connections, and more). This is the simplest but also most common advice I give: if you want to chase an idea, start forcing yourself to talk to people about it.
  2. Learn the field, often shamelessly. In my case, I was launching a business in an industry I knew very little about, so my early learning was critical. I’d use my lunch breaks to cold-call fabric manufacturers, trying to better understand the world of antimicrobial fabrics. I’d ask wildly simple questions of salespeople, and end calls requesting sample swatches. I started to build a foundation of concepts and jargon quickly, and worked to build a mental map of the production process.
  3. If you’re able, set aside some working funds. About 2 months into the idea’s existence, I moved money into a separate checking account that I named “entrepreneurship fund.” It didn’t need to go to this specific idea, but it was money earmarked for learning and experimentation. This allowed me to spend confidently within a boundary, rather than belaboring each early investment decision.  

How did you validate your idea before going further?

This is one of the most common questions I get, and one I relate to so deeply. At its core, it’s a manifestation of fear: a fear of wasting time or money, a fear of pursuing a “bad” idea, a fear of having missed a key signal early on. And while I totally get it, my response is somewhat stark on this one: there’s no way to truly validate a physical product idea without producing a physical product.

To be clear, that’s not to say, “dive in fully and never look back.” My approach was quite measured at the start, and I intentionally built my business around small, local production runs. I started small to validate, and expanded my inventory and offering as I further learned from customers. This kept my monetary investment within the bounds of my “entrepreneurship fund” while also letting me test out my production process end-to-end.

The reason I say there’s “no way” to fully validate is because I think many entrepreneurs are hoping for a secret path that lets them avoid the challenge of production. They ask about testing ads with stock photography, or building a bunch of fake door tests into a website. Yes, these strategies can be informative, but they’re not going to give you the full sense of whether or not your idea is a good one. I’ve run a lot of A/B tests in my career in tech, and I’ve learned time and again that any test result is an assessment of both the hypothesis and the execution. In the world of manufacturing, I believe execution needs to take the form of some physical product – it could be a single sample or prototype – for you to really learn. 

How do you think about building your business full-time vs. as a side hustle?

Weeks after I first launched First Peak, I wrote a post about managing a side hustle while in my full-time job. I focused on how entrepreneurship made me feel more focused and energized at my 9-5, and how I hoped more people (especially women) would consider taking the plunge. 

My professional responsibilities since that post have changed significantly: I took 15 months to travel with my family, leaving that 9-5 job behind. During our travels, First Peak was my primary “work” – I used the travel experience to inform the brand, and I built out production from the road. 

After our travels wrapped up, I moved back to San Francisco and decided I wanted to take a different approach and not return to a conventional full-time role. I crafted a workload of contract consulting jobs, where I support 2-4 companies at a time, and set aside explicit bandwidth for First Peak. This has allowed me to stick to the tenets of my initial “side hustle” post – pursuing work that energizes me, advocating for my own needs and boundaries – while also maintaining both independent and collaborative environments, and fostering a steady income stream.

To put it simply, I like having First Peak operate as a side hustle, and I’ve listened to that preference, even as my work responsibilities have evolved.

How are you managing the business with a new baby at home? How has your approach changed?

Being a mom and being an entrepreneur have always felt inextricably linked to me: First Peak was inspired by my son, and the business has been a vector for so many of our adventures as a family. That said, baby #2 has certainly shaken up my perspective. I launched First Peak with a 1-and-a-half-year-old at home, which feels very different from launching or managing a business with a newborn. Sleep deprivation and physical toll alone have forced me to step back and reassess my near-term goals.

More concretely, looking ahead to 2024, I’m thinking far more about stability and profitability than I am about growth. I’ve shifted my goals toward building a business that can be self-sustaining (e.g. bringing on wholesale partners, tightening up my production processes, doubling down on my top products), rather than hinging success on vastly expanding revenue. This doesn’t mean that the work is now necessarily easier – I was still picking up dye orders at 39 weeks pregnant and visiting the factory 2 weeks postpartum – but it does feel focused and aligned with where I am personally. Introducing a new baby to our family is a broader journey of adjusting to a new normal and finding stability through many challenges; it feels far more consistent for my business to be doing the same. 

Are you enjoying it?

I often chuckle when I get this question because I sure as hell better be! Entrepreneurship is far too hard to be worth the effort if it’s not enjoyable. 

From the beginning, my goals in building First Peak have been primarily around learning: learning how clothes even get produced in the US, learning the logistics of opening a business, learning how to coordinate partners in an industry totally new to me. These goals have kept me grounded, and have allowed me to enjoy the journey as much as the outcome. 

That’s not to say there aren’t low moments. I maintain a checklist on my laptop titled “shutting it down,” that includes all the steps I’d need to take if I wanted to be done with this business. There have been many days where I open it up and contemplate how I’d feel if First Peak was no longer part of my life. But for all those low days, there are far more energizing, creative, and joyous days. I’ve learned that I’m happiest when I’m creating new products, and I’m strategic about maintaining space for the creative work of building and designing. I know that I light up when I'm meeting new families, so I consistently solicit feedback and reach out to customers. I’ve also learned that great partners make everything more fun, and I’m deeply choosy about whom I work with. 

There are many questions I didn’t include here, but I figured this post was already long enough. If there’s something I missed that you’ve wondered about, I’d love to share more. 

And I can’t help but end this post with a little emotional gushing, to express the immense gratitude I feel to still be building First Peak two years in. So many ideas don’t make it this far, for reasons in and out of our control, and I feel truly lucky that entrepreneurship continues to fuel my creativity, that my husband and kids have been such supportive helpers (and models), and that families continue to find and take a chance on First Peak. 

As with any small business, the best ways to support are to shop, share, and engage. Simply by reading this far, you’ve already done the third, and for that, I thank you. 

To many more years ahead! 

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