All the Stuff I Got Wrong in 2019

Sharmadean Reid MBE
15 min readFeb 10, 2020

Whew chile! 2019 was an… interesting year. Was it the planets? End of the Decade? Who knows, but everyone I know seemed to find it challenging.

At the January edition at our regular Women In Tech night, held at the Beautystack HQ, I shared my top 5 mistakes of 2019 to an audience of 100 Women along with a few other female founders. While we had Chatham House rules, I thought it might be worthwhile to put them in print, with a few more reflections…

Excuse the typo…

Almost every mistake I made could go back to “Playing CEO” What do I mean by that? Well I could go back even further for my first mistake:

1 — Don’t raise more than you need Pre-Product Market Fit.

Exactly a year ago we raised a large seed round. We had inbound term sheets, it happened all rather quickly and wonderfully, but in my initial plan, I thought I’d be going out to raise half of that a little later. I’m not sure where this figure first came from, but we did it. It gave us a very long runway which was super positive, and I was grateful to have one of the best funds, and most supportive and experienced investors on my board. That said, it completely changed my mindset. It meant I had to spend it and I got too comfortable and lost the sense of urgency. I had to hire, I had to create processes, all for the money, not the product. It stopped me thinking like a Founder and more like a money manager. I had to manage this money and allocate resources. Which doesn’t make sense, because before you reach Product Market Fit, you’re just trying stuff out, you don’t know what to pour the money into. You know what I should have been doing???

2- Stay a Founder as along as possible. Don’t play CEO

What I should have been doing is staying as close to the product and users as possible to find PMF. You think you can do that after you’ve raised a bunch of money. I certainly intended to do that, but instead you’re sorting out employee contracts, office leases, creating employee onboarding processes building our team structures, sorting out away days and strategy days and doing constant 1:1s to ensure everyone is aligned. It’s all just processes to grow a company, not building a product to grow a business.

The fact is, I’ve never scaled a company before. I’ve never actually grown anything before, apart from an Instagram account. While I’m often lauded as a business inspiration, when you think about it, I’ve only ever hired nail artists and ran a single salon (debatingly) effectively. I’m a Founder learning to be CEO. And being a Founder is what I love the most. I’ve always been someone who sets stuff up, started things, got people together. I always have a clear vision, I have product taste and I love building communities.

So stay a Founder, keep your team small and tight. Sit around a table and be immersed in nothing but the product and user feedback. Management slows you down, and we were too small and too early to be slow. My ideal work environment is a University classroom, so keep it that way until you hit Product Market Fit. Do the paperwork and processes at night and do all the thinking work in the day. Start a project and nurture it. Growing Companies? Still figuring that one out…

3 — Stay small for as long as possible.

Because we raised all of this money, and because it meant that funds believed in us, I felt a lot of pressure to grow the Company. I went out and hired like crazy. And because I hired, I had to manage. And because I had to manage, I wasn’t working on Product. And because I wasn’t working on Product, I had to hire Ops to free up my time to attempt to work on the Product etc etc…

Founders are just as responsible to each other for this pressure. When you’re at a dinner party and you talk about your Company, the first thing people say is “How big is your team?” or “How many people have you got?” like having more team members is a badge of honour. Let’s stop doing this to each other! Well a mistake I made was hiring too fast, having no method to hiring and hiring randomly.

We ballooned to 25 people by summer, but no Senior roles, so we had many junior and mid level and inexperienced team members needing direction. Either inexperienced in the role, or inexperienced at a start up environment and some folks were just inexperienced at small business — which is chaotic. I began to feel like I was managing everyone. I was grouchy, rude, stressed, snappy. I wasn’t doing my favourite type of work at all and I wasn’t being my favourite type of person. It was tough for myself and everyone around me and now is a good time to apologise for that.

I realised that while I can be a good mentor and an inspiration to many, I’m actually not a great individual coach when people are struggling with their work, particularly with junior team members, I’m just too impatient. This phase helped me learn a lot more about myself. The type of work I like doing and the type of people I like doing it with. I like sparring partners, I don’t like to micromanage or dictate. I don’t feel comfortable with those who are eager to please me as their leader, rather than please the user or change the world through our mission. If a dynamic starts to emerge where someone is losing motivation in the mission, I can inspire, but if they’re losing performance, I get a bit lost. To combat this, I hired a Coach for the whole team in the form of Jess Ratcliffe, so they had someone apart from me, to talk to twice a month. But even so, I tried to figure out my contribution to team issues. I spent most of the latter part of the year in this quandary.

In fact, I even found this in my notebook (I think in diagrams)

So partially to reduce our burn and partially to create space for more experienced people, we halved our team by the end of the year to just 12 people. My advisors and investors verbally patted me on the head in an endearing way as if I’d went through my first defining Founder experience. My Founder friends a few years ahead of me laughed at how stressed I was and just said “It happens”! But for me it was one of the most testing mentally anguishing years ever (more on that below).

4 — Hire for goals, not roles.

What could have helped was to have only hired proven experienced people. I mean truly experienced, like they’ve done the role at least 2/3 times before, been at a start up and are looking for a new culture, new product, new challenge. My goal for this year is to hire Senior team members who can push me, feel confident to challenge me, and build their own teams from the ground up. Hires who are hungry and just killer, no filler, who can support me as I continue to learn to be a CEO. It takes a lot longer, but I’m confident it will be worth it. BTW — if this blog post doesn’t scare you, you’ve got 5+ yrs Senior experience in Ops, Product or Engineering and you’re down to economically empower women globally, HMU.

Once you have experienced, ambitious people, just set them a goal, not a job spec. Alex Dunsdon says it best.

In these early days, I’ve realised those who need a job spec, probably weren’t right for my stage. (I’ve wasted so much time writing Job Specs and Org charts. Playing CEO!!!) If they needed rules and over process and management, they’re gonna be great for when we are further down the line, not right now.

Michelle You, coFounder of Songkick and LG VP told me about Jungle Mode (can hack through anything), Dirt Mode (can make a path from the dirt) and Super Highway (can scale), to describe 3 buckets of hires who help you on your journey. Some people call it Explorers, Town Planners and Homesteads. The point is, the mindset to achieve and the tendency to DO rather than MAKE DECKS is key.

I don’t think we made bad hires, I’ve loved getting to know and build relationships with everyone we have hired, they were just not right, right now.

Having said that — the opposite could also be true. Some of our longest hires had never done their role before, but they had a genuine growth mindset and proved value through action.

I’m sure there’s so much more I could write on this but just remember to keep the team small and hire people who are on your level and know more about their job than you do.

5 — Stick to What you Know or There is no need to reinvent the wheel.

Because I’m so obsessed with new, next, innovative, I worked so hard to “Play Tech CEO” and do lots of fancy things in my product that no one actually asked for. There was actually no need to reinvent the wheel for 80% of our product. There are multiple SaaS booking systems that do the job perfectly fine. While I think scheduling is a dated problem, it means that other companies have had 10–15 years to work on it and we can learn something from them. We have two key functions that define Beautystack: network effects and booking via UGC. Our Millennial and Gen-z audience, business model, growth loops and acquisition model are what defines us and differentiate us. Our user insight and my experience within the Beauty industry set up apart. If I stuck to what I know and do well — connect a client with a beauty pro manually, I mean, if I’d literally just opened a salon for all services and built some old school software in my cool way in a VC backable model, it would have been a significant step forward for the beauty booking industry.

But trying to be too extra, not having experienced Product Management and no one to challenge my assumptions meant that we got to our progress a bit slower that I’d have liked.

That said, even with a limited product we grew a quarterly average 33% last year in GMV and Bookings! But still, in my heart I know we have a long way to go with our product and so many exciting opportunities to tackle.

So just think — are you trying to reinvent the wheel here? Why did your investors choose you? Why did you users choose you ? Can you do what you do best, but apply a start up methodology to it?

Towards the end of last year, I switched gears, held some events, connected users with their favourite pros on Instagram and text and the conversion was amazing. Change your industry incrementally, do what doesn’t scale and then figure it out, rather than skip all the steps and attempt to build the whole future, today.

6-I let other peoples opinions sway me. Especially those who had never run a business before.

When things are good, no one has advice, but when you have a problem, everyone has something to say. And when you don’t even have a problem, there will be haters and critics. The hardest thing to learn was how to parse the information you’re getting. What do you do when someone tells you what to do? I was taking hiring advice from people who had never hired, business advice from people how had never actual run a company before, and getting upset by people who just couldn’t empathise with my experience. I was just generally getting more and more confused and a bit lost about the direction to take.

Arthur regularly sent me this famous speech which has been my rallying cry for the year and Ross sent it to me again recently.

Ultimately, I have a mission and as long as I’m not hurting anyone (including myself) along the way, I need to stay blinkered and focused on doing this, because not everyone is willing to step into the arena.

The one trait I am grateful for, is my ability to wake up every day and start again. It’s so easy to get swayed on your start up journey. Stay strong and find your peer group to support you.

7 — I isolated myself.

Which brings me to my next point. I was feeling so low, and getting so stressed and depressed that I began to isolate myself from people. I didn’t really reach out to my investors for help. I stopped going to the Foundrs Tribes, I started at a Local Globe PEG Group then dropped out (they’re both amazing YPO style peer groups) For the whole of 2018 I hosted a weekly dinner party at my flat, in 2019 I didn’t host a single one. I stopped doing meet ups, Future Girl Corp and reduced my panels. I stopped going to see my best friends in New York and LA. I stopped writing my newsletter. Hell, I even turned down a solo WIRED UK cover 😭 because I felt like I was a fraud and everything was going wrong!

I didn’t go to many meet ups, dinner parties, industry events, or when I did go, I didn’t talk to anyone. I just started acting weird. I’m a Gemini! Socialising and hosting is what I do! But work was just making me feel meh.

I had done this before when I was lost, for a few years I went back to Wolverhampton and didn’t really engage with my best friends, because I was feeling out of sorts. But this time I couldn’t run away to my hometown. I came to my office every day and every evening just went home and pottered around.

Any mental health professional will tell you this is Number 1 thing to NOT do. So for 2020 I vowed to be more active and vocal in the London Founder community. Already in January, I met with my LG and Index Portfolio members, rejoined Foundrs, I’ve done my Somers Town block walk with Saul Klein and I’m starting my Friday night dinner party again. This week alone, while reaching out for Board Prep help, five founders have spent time with me, making me feel incredibly supported.

My female founder crew of Michelle Kennedy, Amy Thomson, Poppy Jamie and Kharmel Cochrane have been my life line on speed dial. Cheryl Clements my Coach has got me through. Henry Davis, our advisor, has just been so real and stellar with his words and Arthur Kay has been like a lighthouse for last year. Ross Bailey has been incredible for being a Mr Motivator and Tabitha Goldstaub has just been a voice of reason. Ronen Givon, Kenny Ewan and Mandeep Singh are my LG fam who have kindly spent coffees and dinners hearing my challenges and Valentina Milanova is a new but most welcomed friend. There are people out there who want to help and I’m sure I’m missing many more. I’m grateful for you all.

Isolating myself was a big mistake. Everyone is rooting for you, connect with your peers and find your family.

8 — I forgot the main thing.

I got so bogged down in the stuff above, I forgot what my actual job was. I really believe Beautystack should exist and I really believe there is a new way to book beauty online and unlock earning potential for millions of women. So y’know, I’m just gonna do that and everything managementy can be ignored temporarily.

Okay so now, some stuff I did do right, that might look wrong on the outside.

1 — I closed my nail salon for good.

There are multiple founders in the Local Globe portfolio who ran a logistically heavy “traditional” business that reached a ceiling, gained a user insight and built a tech company to empower others to scale their businesses in their industry. I think it might be part of their thesis…

Some of them sold their business, closed it properly or it failed. My mistake was that I tried to straddle both WAH and Beautystack unsuccessfully. I didn’t manage the salon properly, I let the debts mount up as the business rates in London sky rocketed and I wasn’t around to motivate the amazing talent we had in there.

Just to illustrate how I was balancing two worlds… Just ONE HOUR before I pitched to the partner meeting in 2017 and got a term sheet for a our pre-Seed round, I had to run around to the salon on Wardour Street from our office on Tottenham Court Road and transfer my entire life savings to a bailiff who was standing outside the salon because of outstanding PAYE debts. I was sweating outside the Natwest on Dean St and had to pedal like crazy via Santader Bike to Kings Cross to the Camden Council office to do the Monday partner meet with Local Globe. It was one of those things I might laugh about in the future (when is the Silicon Valley meets SATC show coming?) but all I could do at the time was shrug and keep on truckin!

BTW I still nailed the pitch despite having about £5 left in my bank account :)

Closing the salon in 2019 was tough but it wasn’t just about the money. I could have acquired it into Beautystack or made it work somehow as I had done for the past 10 years.

Closing the salon was about me putting my money where my mouth is and building the future of work for Beauty Pros. The salon model today does not work for most Beauty Pros. Young women pour their money into physical property only to experience crazy rents, increasing business rates and a stagnant high street holding them back. WAH was one of the most famous nail salons globally and we acquired new customers weekly, yet even we found it difficult to maintain.

So closing made sense as I strove to apply my learnings to a more scalable experience. If all my WAH girls can transition to Beautystack, then so can others.

One of our Pros on Beautystack made over £25k this year working 2 days a week painting nails. In a salon she would make 1/3 of that. I didn’t feel comfortable paying these talented artists a Minimum London Living Wage in a salon, so I had to walk the talk and take the big step to closing my shop and empowering the girls individually.

That said, our end product still happens IRL. The app facilitates an actual physical connection so the salon experience will have to happen in some form or another, but it has to evolve from its present day incarnation.

Look out for another blog post of why I think salons as we know them will die over the next decade.

2 — Got a big office

Our office is way too big for our now tiny team but it was worth it. The vibe is fantastic, the space really sets the tone of the brand and more importantly, we can hold events in here all the time. Events generate bookings for us. We aim to have 200 Beautystack Users through the door every month which we then convert to book through codes and surveys. I built the cost into our financial model from the outset and I’ve never regretted having somewhere beautiful to work every day. I spend more time in my office than anywhere else and the team are happy and productive here.

I’m sure there are more lessons, but these are the ones that I managed to reflect on and get through. These are the ones I feel much better about, the ones I got over.

I know its a rollercoaster journey, but I didn’t plan for needing a tighter seatbelt. It’s been wild but a learning experience and I’m still alive! They say hindsight is 2020 and in truth, I can only write this having gotten through the fog. If you have a Founder friend showing any of the above signs, reach out and offer some support. It’s one of the loneliest jobs around.

Here are a few things that REALLY helped me through this bit:

  1. The Messy Middle — Scott Belsky
  2. The Hard Thing About Hard Things — Ben Horowitz
  3. Listening to Recode Decode.
  4. Having a List of Things That Make Me Happy…that i refer back to when shit gets tough.
  5. Always always listen to Hip Hop. It’s keeps the hustler mentality within you.