Alright – so today we’ve got the honor of introducing you to Skyler Kroschel. We think you’ll enjoy our conversation, we’ve shared it below.
Skyler, looking forward to hearing all of your stories today. Almost all entrepreneurs have had to decide whether to start now or later? There are always pros and cons for waiting and so we’d love to hear what you think about your decision in retrospect. If you could go back in time, would you have started your business sooner, later or at the exact time you started?
Starting my photography business during the pandemic in 2020 was a pivotal moment for me, but there’s a backstory to it. Around 2016, fresh from a transformative year in Southeast Asia, I attempted to kickstart my photography business. However, I was naive and lacked the necessary skills. Despite offering free photoshoots, I struggled with both capturing quality images and navigating the business side of things. Eventually, I let the idea fade away, overwhelmed by the challenges and uncertainties of entrepreneurship.
Fast forward to 2020, amidst the pandemic, I found myself reevaluating my career path. The dormant desire to pursue photography resurfaced stronger than ever. With more maturity and determination, I dove back in, juggling it alongside my job as a Montessori assistant teacher. This time, I approached it with a more strategic mindset, investing time in courses, practice, and legalities to establish a solid foundation for my business.
Reflecting on this journey, part of me wishes I had persisted in 2016. Perhaps starting earlier would have given me a head start in an industry now saturated with talent. Those who embraced social media and entrepreneurship earlier seem to have gained a significant advantage. While I’m proud of my progress, I can’t help but wonder about the opportunities missed by not fully committing earlier.
Ultimately, every step, whether sooner or later, has shaped my journey and contributed to my growth as a photographer and entrepreneur. The lessons learned from both attempts have enriched my perspective and fueled my determination to succeed. So, while I may ponder what could have been, I’m grateful for the path that led me here and excited for the future it holds.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.
Skyler is an intimate wedding and family photographer for the wild and carefree. Based in San Francisco, I’m passionate about documenting memories in the most authentic way possible. If you’re looking for images where every finger and hair is in place, I’m not the photographer for you. I work with clients who want more than a perfectly posed picture; they want an EXPERIENCE, an opportunity to be themselves, have fun, and to know that their story has been honestly and beautifully frozen in time.

Can you tell us about a time you’ve had to pivot?
Oh, there are so many moments where I’ve had to pivot, but one that stands out is when I initially resisted photographing weddings. At the start of my career, I was adamant about not including weddings in my portfolio. I perceived them as high-stress and not aligned with my artistic vision.
However, when a close friend asked me to document their California wedding, I faced a dilemma. Despite my hesitations, their unwavering belief in me pushed me to accept the challenge. With some guidance from a seasoned photographer, I reluctantly embarked on this new territory, bringing along a second photographer just in case.
The experience was, to put it lightly, nerve-wracking. I struggled feeling the weight of the responsibility. But amidst the chaos, I managed to deliver photos that pleased my friends, even if I didn’t enjoy the process.
Just when I thought I was done with weddings, another opportunity arose when my cousin asked me to document her special day. This time, armed with the experience from my first wedding, I took on the task solo. Determined to excel, I poured my heart into capturing every moment.
Surprisingly, with each wedding I photographed, my confidence grew. I honed my skills, discovering a particular fondness for San Francisco City Hall weddings for their brevity and intimacy. Through perseverance and adaptation, I transformed from a reluctant wedding photographer into someone who embraces the challenge and joy of capturing these cherished celebrations.

How did you build your audience on social media?
Social media is a beast. My determination in this realm constantly ebbs and flows, with me determined to give it more of an effort one day to hardly caring about it the next. While I do think it’s an important part of business, I also think it’s a huge energy suck for many people. If you don’t feel inspired or excited to share on social media, then you’re either sharing too much or not the right content. Yes, it’s important to sell on socials. However, I know so many successful business owners who hardly use social media. Rather, they nurture their email list or focus more heavily on SEO and running ads. In the end, you need to find out what works for you. And don’t worry if you don’t know yet. I’m four years into business and I’m still figuring it out myself.
If you’re determined to grow on social media, consistency is key. Post to IG stories every day (make sure your FB account is connected), post frequent reels (at LEAST 2x per week), use relevant hashtags, and share content that’s actually useful to your audience. It may take a while to get the ball rolling, but if you’re consistent and putting out quality content, you will grow in time.
Contact Info:
- Website: https://skylermaire.com/
- Instagram: https://www.instagram.com/skylermairephotography/
- Facebook: https://www.facebook.com/skylermairephotography/
- Yelp: https://www.yelp.com/biz/skyler-maire-photography-san-francisco
- Other: https://www.pinterest.com/skylermairephotography/

