A Peek into My Business Stack as a Product Coach & Consultant
BTS on where I succeeded and where I went wrong in the first year of creating a business stack
Last week, I shared frustrations and myths of self-employment, with candid insights from the early days of my journey. Today1, I'm circling back to provide helpful reflections for fellow solopreneurs. This one's for you, Erin! And you too, Josh.2
It’s a mini retrospective on the first year of my business stack, specifically: where I succeeded and where I went wrong to save you from making the same mistakes I made along the way
First …A note on how I used my product manager brain to make decisions
Similar to launching a new product, I kept experimentation near and dear, constantly checking myself on how and when to be scrappy. I applied these three principles to whatever decision I made, and I believe, it’s served me well:
Focus on building relationships and honing coaching skills rather than perfecting my business or tech stack. As a true product manager, I focused on finding product-market-fit before building the whole kit and caboodle3. I can’t imagine how disappointing it would have been to build out all the processes, paid for all the software only to find that I was miserable coaching people everyday!
Use familiar tools to ease onboarding discomfort. I get cranky4 when I have to learn new technology, despite having worked in tech for over a decade. It’s honestly a little embarrassing. But, with this self awareness, I didn’t push myself to onboard onto all new things, all at once. I stuck with what I knew and what made me feel good. You’ll see that below.
Wait until things break to scale. This one’s a bit arbitrary but rather than plan for systems to break, I waited for things to break. I even found I could go pretty far with some things that seemed like they’d be laborious (i.e. invoicing 10+ people only took about 30 min a month). But, eventually all things break if you’re trying to scale. My biggest advice: be aware of your breaking points and don’t ignore them.
Disclaimer: These principles are based on my experiences and may not universally apply to all businesses. Because, duh.
Ok, onto the good stuff…
A Retrospective on my Early Decisions
Reflecting on the first year of self-employment, here's what worked well and areas where improvements could have been made:
What I Did Well
I delayed creating a website - Instead, I initially opted for a simple Google Doc and my LinkedIn page to sell myself and save my time and resources. It lasted me about 5 months and it worked just fine. It also saved me from trying to lock in my “brand” too early.
I forewent a contract: In the beginning, because I was so new, I decided not to include a contract. Why? Well, because writing a contract isn’t the easiest thing to put together (even with 3 lawyers in the family). Eventually, I introduced it as my packages and pricing structure changed. Now, I view it as an important formality that strengthens my client relationships.
I promptly filed my LLC: I filed for an LLC early on to formalize the business structure. I’m happy I got this out of the way immediately as it enabled me to take other actions easier. It also made it “official” in this really non-important but maybe important kind of way.
I set up a business banking account + credit card: I chose a dedicated business checking and banking account to immediately separate my business and personal finances. More on what I chose and why below.
I consulted with my accountant: Seeking advice from a trusted source, my wonderful Father-In-Law, David, streamlined financial decisions in the early days of business. I had no clue what my tax situation would look like and having conversations early eased some of the anxiety early on.
Areas for Improvement
Getting a work email - I wish I got my work email, through google workspace, established sooner. Today, I’m untangling my personal email from my work email and it’s not a great separation of “church and state.”
Standardizing Payment Method - Though I knew the need for a consistent payment system was crucial, I didn’t prioritize it early because I wanted to stay flexible for my clients. I wish I stayed firmer on that earlier on. I’m only starting to standardize now.
A better email tool - I relied on free email tools, like Substack, and I wished earlier on that I had chosen a robust email distribution tool for efficiency. I’m doing that right now…sigh
And now, a comprehensive overview of my current business + tech stack
Hopefully obviously I am not affiliated with any of these companies or tools so all my endorsements are authentic AF. But Loom, lmk if you need a new influencer?
Free Tools That Keep Me Grounded
Trello: My Long Time Friend
I've utilized Trello since my AOL days. Its familiarity and versatility made it an obvious choice for a CRM. Now, it’s an integral part of my daily operations, especially for client management and networking calls.
G Suite: My Comfort Zone
Meet: My preference for meetings leans towards Google’s Meet. Its simplicity and efficiency outshine other options, making it my go-to over Zoom.
Gmail: Gmail remains a stalwart in my toolkit, managing communications seamlessly and serving as a reliable inbox. My last job required Outlook, so I’m so happy to be back on Gmail.
Google Appointment Booking: This tool allows me to create multiple appointment calendars for free, offering a streamlined scheduling process. Its integration with my calendar is a game-changer. I love it so much. I bet they will make it paid soon. But please don’t, Google!
Google Drive aka Organization Nirvana: Google Drive is my organizational haven, ensuring easy access to all necessary documents. It’s not official until its in my Drive.
Substack: My Medium Replacement
Shifting from Medium to Substack was driven by its more buzzy appeal, but it's proven glitchy and headache-inducing. And these days, morally problematic? A migration is on the horizon. Watch this space.
Slack: My Community Builder
Slack was a no-brainer when Connie and I dreamed up a coaching community. Its free product delivers everything we need, and we've found a clever way to archive content on Notion as a cost-saving work around.
Loom: My biggest shortcut
Loom has been a revelatory tool for sharing plans, reviewing resumes, and explaining concepts visually. It's become an invaluable asset and I’m kind of obsessed with it.
LinkedIn: My Biz Dev Bread and Butter
LinkedIn has been my primary tool for business development. Though I finally tried Premium this month, its impact has been less riveting than expected. I’m cancelling my trial this week. 😬
ChatGPT: My Personal Writing Assistant
As my writing assistant, ChatGPT plays an increasingly significant role in my daily tasks - more on that here. A world where I pay for AI-generated imagery might not be far off. I’ve tried Bard but ChatGPT “gets me” more.
Canva: My Visual Content Creator
In less than 24 hours as a Canva customer, I’m obsessed. Without brand photography for my coaching business, it’s produced professional, on brand materials for me to promote my workshops with. It’s also very fun.
Paid Tools Elevating My Game
Squarespace: My Online Presence
Despite a few kinks, Squarespace gets the job done in terms of website design. Its user-friendly interface and forward-thinking integrations align seamlessly with my needs. I debated going with other options, but everything kept falling short compared to Squarespace.
Paperbell: My Streamlined Coaching Processes
Paperbell is my recent investment, streamlining coaching client processes—from payments to contracts to scheduling. So far, it's been reliable. I liked how small they were and was hoping that their customer support experience would be more personalized because of it. As of the first few weeks, it’s delivering.
Chase: Banking Convenience
Prioritizing familiarity, I opted for Chase for all my banking needs, steering away from enticing alternatives like Mercury. I needed seamless transfers and quick overviews of personal and business, and since I bank with Chase, this one was a no brainer.
ConvertKit: Email Optimization
To enhance my email game, I went with ConvertKit (over options like Flodesk, Beehiiv, Mailchimp). Its capabilities for tagging, sequencing, and segmenting have impressed me, despite slower customer support.
Business Coaching: My Personal Coach
Investing in a business coach was a big decision, but I think it’s already paying off… pushing me to refine my writing, marketing, and sales strategies. As I know from my clients, there’s nothing like paying for something to create accountability and change. LFG.
Zoom: Workshop Hosting:
As I venture into workshops (check out my upcoming one here), Zoom became a necessary tool for hosting sessions with large groups, surpassing Google Meet in this regard.
Experiments That Didn't Stick
RIP to the software I tried. You may be great but you weren’t for me.
1. Honeybook: A clunky experience
Despite many recommendations, Honeybook proved clunky and confusing, demanding extensive onboarding without delivering user-friendly results. If you have to watch more than an hour of onboarding videos and still don’t get it, that’s a no from me dog.
Calendly: Gated Functionality
Calendly's clunky and gated functionality led me to explore other scheduling options that offered more flexibility without additional costs. Google Appointments forever!
Notion: Yet to Capture My Heart
Despite the popularity and absolute BUZZ of Notion, my heart remains with Google Drive. I wonder if Notion will one day sway me?
This business stack represents my ever-evolving toolkit. For those on a similar journey, I hope these insights help you curate a stack that empowers your success. Onward and upward!
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Are you a solo entrepreneur or considering going solo? What tools do you use, and what lessons have you learned?
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A public acknowledgement and apology to my husband. Thank you for your continued patience.