How to find the time and money to start your business.

Part 2/8 in a series for early-stage founders. Exploring quitting your job, managing your financial runway and finding conviction in the process of starting.

Welcome 👋

We’re continuing an eight part series on how to make your new business a success. The next two weeks; the practical side of starting out in terms of time and money.

Do you have enough cash to support yourself whilst you launch your business? Do you know how much money you even need to do it?

Getting these things right ensures that you can take the right steps to make your vision a reality.

Vision without action is merely a dream. Action without vision just passes the time. Vision with action can change the world — Joel Arthur Barker.

But action is only possible with a plan.

One of the most common challenges I hear from ambitious people who would love to run their own company is their practical considerations stand in the way of planning.

Concerns such as

  • “I want to get on the housing ladder but mortgages are harder for self employed people”

  • “I need a steady income to take care of my family, I can’t just quit and pray my business works — it’s too risky

  • “I’ve got debts / loans to pay off, should I sort these out first?”

So whilst this post cannot answer every single concern it will share some creative solutions for making it work. With special consideration of personal finances. Which, by the way, is intrinsically linked with timing because when you work on your business depends on your other commitments such as having another job.

Without stating the obvious, none of what I write constitutes as financial advice so please do your own research and make informed decisions!

P.S if you want details on whether or not to raise money we’ll be covering that in a few weeks.

And if you’re not subscribed yet, I write career advice for entrepreneurs every Wednesday. Join a community of people creating income from doing what they love.

Andrea Desantis

In this post I’ll cover:

  • My own story, and what it’s taught me about the practical side of taking the leap

  • Case studies of my clients who have made it happen in their own wonderful ways

  • Suggestions and advice for how can navigate the process of starting your business and some considerations along the way

  • Next Wednesdays’ post will be sharing tools and resources for these exact questions

How I started The Ask® in 2020 (despite being a new solo-homeowner, having no business plan or bank of mum and dad).

Remember that I told you about the dream job I had in 2019 that came to abrupt end? It would be a quicker and easier story if I’d started my business right off the back of that experience.

But the reality was that I wasn’t ready to start my business back then.


I had recently bought a home, as a single homeowner I was NOT ready to put that at risk, so I had to go job hunting.

But in September 2019 I landed a new job that was a nightmare.

A story for another day perhaps but after just 10 weeks I had to quit to preserve my mental health. By which point I’d left two jobs in two months so was not exactly proud of the fact, nor excited by the prospect of finding a new one. My faith in finding a job I enjoyed was at an all time low, and this was coming from a Head of Talent who knew a thing or two about jobs. It wasn’t that I didn’t believe I would find one, but that I just didn’t want one.

Sounds like a privileged position to be in?

At this point in my journey, I did not have the mental energy to try my hand at another senior role in tech. So, I gave myself three months. Three months to figure out a plan, to use my savings, to work in bars/shops or temp jobs or whatever was needed to keep the lights on and give myself some space.

But what I did have energy for was committing to a future version of myself. A version of Ellen I knew was in there, who wanted to be a coach.

So I took a bet on myself and signed up for my coaching diploma two weeks after quitting my job.

Bold? Stupid? A mixture of the two I suppose.

But the decision was a force multiplier towards a brighter future.

I quickly landed on my feet with not just any temp job, but a 3 month contract for the prestigious consulting firm, BCG Digital Ventures, on a nice day rate. This quickly paid back for the £4k investment I’d made in my coaching diploma.

Becoming a contractor served another purpose.

Overnight I had to set up a Limited Company, insurance, and business bank account and hired an accountant.

These decisions which may have otherwise taken months of deliberation I had to do between Christmas and 2nd Jan 2020.

Suddenly I was self-employed.

This was not the future I’d envisioned, exactly, however.

I was still working five days a week, going into an office, and had managers, targets and deadlines to meet. My role was also in recruitment, something I was good at but not interested in doing full time.

So in the background, during evenings and weekends I continued to work on my plan whilst also training to be a coach (40+ hours of practice coaching, 8 days of workshops and trainings and essays to complete).

Just as my three month contract was coming to an end, I was approached by a VC backed startup to be the Talent Lead tasked with setting up their early stage hiring which I did for another three months up to June and then did some ad hoc recruitment into the winter of last year. Oyster are now Series B with most recent raise of $50m so this is a pretty cool thing to have achieved despite not really looking for this nature of work .

But remember, I didn’t want to work as a talent consultant or recruiter in perpetuity.

Despite these amazing organisations offering me permanent employment prospects, my gut was telling me to remain self-employed.

Whilst risky, and tempting to get a salary (in the midst of a pandemic, might I add) I tuck to my guns and decided to work on building a coaching practice, which I decided to call The Ask around April 2020.

A throwback to The Ask Instagram feed when I just started out!

Here’s how I had the guts and conviction to build my coaching business and reject traditional employment:

  • Sunk cost of time and money. Investing the £4,000 and six months of my life in a coach training course drove me to apply these skills. I typically don’t do things in half measures so I was able to complete my coach training in record time (fastest in my cohort of 20). Plus I was loving it and felt as though I’d truly found my ‘thing’.

  • Cynicism about the jobs market. A market that required me to fit into a box, a box that wanted me to be a recruiter OR programme manager OR marketeer. I wanted to do a bit of everything I’d learned and apply it to a context where that didn’t make me ‘wrong’

  • Working with a business coach. For four months from March -June 2020 I paid a coach to support me to transition to working for myself and build the mindset, confidence and conviction I needed. There were wobbles along the way but she kept me clear on my vision.

  • The pandemic. Whilst perhaps riskier timing to set up a business, I saw the existential threat as a driver. A “why the hell not” attitude came upon me as it did for many people at this time. Plus the lack of ability to socialise meant that weekends and evenings were spent building the business and creating momentum

  • Savings and a strong money mindset. I was fortunate to have built up savings in the years before I quit my job in 2019. If I had been living pay check to pay check my situation would have ended up very differently. But my savings provided security, and then the 6 months of freelance work in my business bank account was reinvested into building The Ask.
    I am my own VC 😜

  • Early wins. I signed up multiple 3 month coaching clients in my first month of announcing my business. These felt like a green lights and sign I was on the right path.

But these factors alone were not enough. By far with biggest driver for me was a deep seated belief in the kind of business I wanted to build and mission I wanted to serve — to help entrepreneurial people carve career paths that work for them.

I’d known since 2014 I wanted to coach people around their work but didn’t know when or how it would happen. The events of the world forced the decision on me in 2020.

How do other people do it? Some case studies of how The Ask clients have started their businesses.

NB Names and identifying information have been changed to protect client confidentiality.

Henry has been running his business for ten years and still takes on freelance work.

Henry is proof that business is rarely an overnight success, but how faith in yourself and your vision can keep you going. He still takes on 1-2 days work as a freelancer in a field that is adjacent to his hardware business so that his learnings can compound and he can reinvest the money into growing his business.

Emily took a loan from her mother.

After a couple of years working in the startup world living on sweat equity for a business that she was no longer passionate about, Emily was not ready to throw the towel in and get a job, but knew something had to change. Through coaching she decided to launch a new business more aligned to her goals and dreams, but did not want to raise external investment or spend too much time on other work. After much deliberation and coaching the ‘least worst’ option was a family loan. Despite initially rejecting the idea due to her independent streak she realised that you have to be flexible in this business!

Samantha turned her employer into her client and reduced her hours.

After many years working with the same organisation, Samantha had had enough and wanted to work for herself. But as it turned out, the relationships she’d built and skills from this job were exactly what she needed to make the leap possible. Our coaching sessions figured out a plan that involved being self employed, but working with her employer as a consultant, on 3 days per week. They trusted her to get the work done and she could do it with her eyes closed. The two days a week she used to ramp up her business, and ultimately fire her employer.

Johann kept his job but launched a course and consultancy on the side.

Johann didn’t hate his job. In fact he quite enjoyed it. He also had a family of four to feed. Coaching gave him the structure, impetus and accountability to finally launch a course and some consulting slots. He now has paying clients he meets in evenings and weekends and his portfolio investments which, over time, will allow him to transition to financial independence.

These stories are the norm more than the exception and are designed to show you that taking ‘the leap’ when starting your business does not have to be so binary in terms of fully employed or fully self-employed. There are shades of grey in between.

I know stories of others who have convinced their workplace to move to part time before eventually leaving altogether, and others like Steph Smith (works for Hustle and is an indie maker) and Sarah Nöckel (VC and founder of Femstreet) who run thriving digital businesses whilst holding down full time jobs because they love the best of both worlds.

How can you take the leap? Some advice to bear in mind.

Andrea Desantis
  • Know your ‘personal runway’ — how many months you can easily live if you stopped working. It is calculated as a product of the cash and liquid assets you have on hand (things you can sell if needed), any other income sources, your living expenses, and ability to draw on your friends and family in times of need.

  • Time block regularly. Employee, freelancer or full time on your business or not, make sure you are dedicating real chunks of time to work on your new venture. Think entire Sundays for months on end. No one said this was easy!

  • Buy a house first, or in c.5 years’ time. Like it or not, getting a mortgage when you run a business is hard, not impossible, but really hard. So if you have a decent salary from your employer and its a priority consider buying now and making the leap after. If you’re not in a position to buy yet, accept that it may take longer because you’ve put the business first and it may take 5 years from starting to be in a good enough financial position. Or if all else fails, marry rich!

  • Expect to invest your own money. Capital is the lifeblood of companies, and in the early days, you will need money from somewhere. If you can afford it, using your own cash is the simplest bet as it comes with no strings attached and you’ll be savvy in how you spend it. If you aren’t comfortable doing this, perhaps you are not in the right position to be starting a company, or you don’t really believe in your vision. But if you won’t back yourself with your own money, how can you expect anyone else to?

  • Have monetisable skills. I’ll admit it is so much easier to do this hybrid work if you have a skillset that is in demand (in my case tech recruitment) but think about all the other ways you can dip in and out of short term projects to self finance yourself. What jobs have you had that give you innate knowledge or abilities? This might be something you no longer enjoy but its only short term.

  • Avoid debt and credit cards. There may exceptions to this rule later on for example to buy inventory when you are waiting on payments to cash in, but early days without visibility on your runway, this is a recipe for disaster.

  • Research grants, stipends and government funding. Certain schemes are available especially for technologies or innovations, marginalised groups or certain types of ventures. Do research and see what you are eligible for.

  • Ask for favours and use your network. Whether that is to do odd jobs for money to keep your bills covered or to find mentors and people who will help you out for free when you’re starting out.

  • Learn to live modestly. Whatever stage your business is at, there will be times when cash is strapped. So learn to live modestly before you have to and making solid financial decisions that will enable you to be flexible if money is tight.

  • Be patient. If it was easy, everyone would do it. Decide how long you’re going to give your business to work and don’t give up until it does. If you expect overnight success you’ll be sourly disappointed.

Feel free to hit reply and share your unique situation if you want a word of advice or two on how to make the transition or get your business off the ground. Sometimes an objective perspective is what you need.

Looking for more support to create a roadmap to get your business off the ground? Coaching with The Ask is a proven process that enables new entrepreneurs to bring their businesses to life and I can’t wait to meet others who are ready to do the same.

Book a free no obligation consultation with me to make a plan on your venture today.

As always thank you for reading. Hit ❤️ if you enjoyed today’s post.

Next week I’ll be sharing some tools and resources to guide you further plus a Q&A with serial entrepreneur Shaun Gold who shares his own tips!

Ellen Donnelly, Founder + Chief Coach, The Ask.