My first month as an Entrepreneur

So I promised I’ll share with you guys as I navigate this journey of working for myself for the first time in my life. It’s been exciting and super confusing to say the least! From waking up randomly at 4:00 a.m. with anxiety, days at a time, to working a full 8:00 to 5:00 with a tight schedule, my days have had all kinds of interesting patterns.

As you know I have wanted to start my own company for the last 2 years, and had to go through quite the ringer to get my green card so that I could officially launch my business, even though the idea had been in my head and brewing for a long time now. It’s painful to feel so restricted when you know you have a great idea, there is the opportunity and you have the skills to get it off the ground, but are tied down with artificial constraints just because of choosing to live in the place you are currently.

Anyway, fortunately we moved past the barrier in two years and I launched RoomPlays at the end of 2020!

Mindset

So one of the first decisions I had to make was whether it should be an LLC or C-Corp – its trivial to bring this up, but it speaks to my mindset and how it evolved. When you are just starting out you literally don’t know where you want your business to go. When you don’t have a single user or a full blown product, it’s often times hard to envision this idea to be a billion-dollar business… But maybe that was the first mistake I made and learned from. Essentially, an LLC makes sense if you want to stay bootstrapped and just ensure the liability is off of your personal assets. A Delaware C Corp is where you are setting yourself up to raise venture capital and work toward being a multi-million to a billion dollar business. I literally spent a month trying to figure this out because obviously the tax implications are massive and switching between one and the other is not a trivial task. Luckily my husband made the decision for me – And said let’s plan on making this a billion dollar business and so we went with C corp! I know this detail is just tactical, but I share it just to tell you about my mindset when I started off is so uncertain… maybe it’s different for others who really know how to get to that billion dollar opportunity. I wasn’t there and I wasn’t ready dare that big.

Balancing act

So the next big challenge for me was handling work and my own business. If you guys remember my schedule at PayPal where I used to head our entire product team for the customer success agent experiences… My day started as early as 6:30 a.m. I would be on calls all the way till I hit the bed, at times not getting time to even make myself a breakfast or lunch. I loved my job, my team and I would not take any shortcuts ever which made the entire balancing act really really rough on me. And I had to learn the hard truth about running a business.

So I would plan my day such that I would spend my entire day time on my day job and literally 4 to 5 hours right after I hung up my last call would be spent on RoomPlays. But some days I would have a 14-hour day at PayPal and wouldn’t even login to RoomPlays. Despite this awkward and relentless balancing act My business was moving at a pace that was surprisingly rewarding. Not like I was making huge waves but people were joining the platform I was sending out marketing material doing designer podcasts getting bookings and whatnot… It almost seemed like oh I can do this No big deal! I can do what people think is impossible having a full-time job while making my side hustle a successful business…. Until it stopped moving. Around March my health really started to dwindle significantly and I just wasn’t able to give room plays the time and attention and thought leadership it deserved to live. My bookings took a nose dive I didn’t have, no content or posts created, and didn’t show up professionally for my own baby. And that’s when the truth dawned on me.. i can’t grow unless you jump in with both feet.

And truthfully this was definitely not an overnight decision, but I didn’t spend too long moving over it because there is always a good reason to not quit your full-time job that you worked your entire life for. I was doing well at PayPal, had a really bright career ahead of me and… to just throw it all away for a dream? It was like jumping off of a cliff with no parachute.

but my husband has been literally my rock and has been encouraging me to quit for more than 2 years now. And I’m happy to share more about what finally made me take the leap but I’ll save that for another time.

YCombinator

So this happened. I had casually applied to my combinator just to feel what it’s like to go through the application process and even forgot that I sent the application back in March. My biggest surprise was when they called us in for an interview. I was beyond unprepared not even planning to pitch and just felt like what the hell was I doing! Needless to say the interview went okay I didn’t nail it I didn’t get in. But what I did get was for half the effort I put in my combinator thought I was worthy of meeting with. What the hell was I doing shooting the opportunity away? If someone else thought I was worth talking to and possibly investing in why was I not investing in myself? It was time.

Dare to Quit

Once I made the decision to quit it all became so real. A bunch of that moment while I had a vision I didn’t worry too much about how much money I was going to make if this business was going to really be a big profitable business what are my biggest challenges where am I spending my time where do I need help do I need a big team do I need to hire do I need to raise money what is my next step How much annual recording revenue should I be targeting what am I projections looking like what’s my customer acquisition cost what’s my lifetime value How do I increase these ratios The list was endless…

the weight of being on my own start to feel insanely overwhelming and my insanely demanding 14-hour corporate job seemed like the easiest thing in the world! And my biggest challenge from that point was I felt extremely alone… My entire life I worked in large companies so my whole network was filled with people who have never experienced what it’s like to be out on your own.

I started reading all kinds of blogs YouTube videos educational documentaries on starting you don’t company being an entrepreneur how to have a maker versus manager schedule how to prioritize time KPIs working in an unstructured environment and then the biggie the whole black magic behind valuations ans fundraising. And it’s really not been that long but once you get into it it felt like doors automatically start to open up. So from being completely alone for 3 months, I somehow reconnected with some of my oldest friends from undergrad who graciously offered ideas recommendations introduced me to on deck… And today just one month after I quit my full-time job I feel like I have a network, I have people who can guide me, And I don’t feel alone. If I wouldn’t have taken that step I would have been in the cozy cushy place where my corporate job would do great and I would never make a single friend outside and I would never be inserted into this network. This may work differently for different people and I see a lot of folks who have held their full-time jobs and gone all the way to race funding before quitting… I think that’s rare and oftentimes if you are the mean founder you need to show commitment and that you are genuinely in it for the long haul.

Unstructured Environment

So once my day got freed up I had no meetings to wake up to and literally hours of free time I got lazy ! It happens and I think it’s fair to take a few days or even weeks to catch up on all the sleep you’ve not had for over a decade and just enjoy the luxury of waking up without an alarm, enjoying your morning coffee while watching your pets roll around in the lawn in the backyard, Taking your time to make breakfast maybe meditate squeeze in a gratitude practice and then begin your day at 9:30 a.m.! This morning routine has been non-existent for me for the last 5 years that I’ve held leadership positions in a corporate job. It seems so simple to ask to just enjoy a couple of hours of the morning for yourself.. but it’s been an impossible race to keep up with overwhelming schedules that you have no control over. So yeah I did take a couple of weeks to take it in and just plan my day between 9:00 to 3:00 and give my body a break.

Pretty quickly that window down and I start to feel my day up with meetings outreach newsletters KPIs monthly road map planning run the business tasks etc. It looked like a lot to handle on notepads and Google sheets. So I started to use Monday.com and it’s actually been life-changing because I actually have multiple dashboards multiple projects to work through and plan my most important tasks.

Here are a few things a do now:

• TMIT – Three most important things I must get done each day. This helps me become really intentional about how I want to spend each day that I work on my business. It can spawn anywhere from tech strategy networking researching just called emailing and whatnot.. but it’s three things that I make sure I accomplish over everything else.
• Multiple Hats – pretty quickly I realized that I tend to gravitate toward product and tech. That’s my sweet spot every time I have to conduct user interviews in corporate feedback I go deep into the product start making mock-ups and you exchanges and code changes which takes up pretty much the entire day. As an entrepreneur you need to break up your schedule such that you are a technologist but also wearing the strategy heart one day working on marketing another day on outreach another day I’m just operational stuff like QuickBooks, paying my vendors etc .. So really it’s one person doing 7 to 8 functions each week. So I try to break my week up in a way where I am a tech person on Monday strategy on Tuesday business on Wednesday operations on Thursday and a mix of execution and marketing on Friday… And Saturday I tried to catch up on anything that I have missed take a whole bunch of calls and stuff but not a lot of hands-on work. I try my best to not do a lot on weekends, it’s hard to stay away but I try to minimize how long I spend on RoomPlays er I will mostly spend the time researching studying learning instead.
• Monday.com – I got into the habit of doing monthly road map planning now and this forces me to plan out my deliverables just like I would at work. I scoop out days where I want to get an Instagram ad live or want to send out a newsletter two more strategic things like getting my pitch deck ready having my business plan flushed out, planning my content & editorial calendar, SEO backlink submissions updating projections etc.
• Building Team – as I’ve got into doing some of these tasks I realized which parts I absolutely do absolutely need to outsource and seek help from experts. Since I’m bootstrapping I’m obviously very thoughtful about where I put my money but this very quickly became a necessity and starting to build out my team has been my number one priority. It’s hard when you are trying to get the product running as well as trying to get customers and designers as well as raise funds as well as network as well as building.. sounds like a lot right? And it is! So the sooner you build a team the better you can do all the other things and truthfully took me a while to realize that I should be prioritizing building a team over everything else but there’s only so far you can go on your own, And the sooner you realize it the better. So I started making my hires experimenting with different types of talent and I feel like I’m working toward understanding what gaps I need to feel right away versus who I can bring on at a later point to help with the business.
• Fundraising – I didn’t think this would happen so soon but I’ve already been meeting investors and it’s been going well! I went through creating my pitch doing my first pitch event meeting and pitching to investors already! Sounds so crazy but it’s all happened just after I decided to quit… I feel this would have never moved this quickly had us so been at PayPal. I know I keep going back to it but it’s just crazy because the moment I chose to quit things just started snowballing!

So that’s in a nutshell what I’ve been doing and learning over the past month or two. Although I felt I was so unprepared and I still do I realized the most important thing you can do at such an early stage is to relentlessly network.. meet more founders go out to events talk to them share and learn from their journey if nothing at this stage just hearing repeatedly that it’s okay it takes time you need to build patience and resilience and in the end of the day you’re not in it for a specific outcome you’re here to enjoy the journey.. to have the grit and the passion to break out of the norm, take the sleep and see your life takes you! End of the day I can always go back to a corporate job that’s my least common denominator. Everything else I get to do is a bonus!