I recently wrote about 6 lessons from my side hustles. Now, engagement has been great (thank you) and many of you requested that I put a bit more detail around each side hustle, why/how I got into it, the business model, some pros and cons, plus a lesson explicitly from it.

So (as a reminder)… this is a rundown of the side hustles:

  1. DJ – main income, not side hustle (retired ;)) Check me on Spotify if you’d like.
  2. Record Label – business, not side hustle (closed)
  3. Bag hire company – eCommerce side hustle (closed)
  4. Chocolate fountain hire company – cash flow side hustle (closed)
  5. HMO management company – cash flow side hustle (sold)
  6. Property sale lead generation business – cash flow and wealth building side hustle (active)
  7. Property management lead generation business – cash flow and asset building side hustle (active)
  8. Investment affiliate site – cash flow and asset building side hustle (active)
  9. Business lead generation site – cash flow and asset building side hustle (active)
  10. Marketing software – asset building side hustle (active)
  11. Serviced Accommodation – cashflow side hustle (active)

Before we go into them individually, you’ll probably also notice that very few exchange time for money. 

I’m not taking a second job. I’m actually investing time (and money) before i get paid in most of these.

I’m interested in building income streams, which over time can scale and become more passive.

So, here we go one-by-one through them all.

DJ and Record Label

Now, these weren’t technically weren’t side hustles as they were my full time gig. But, I think they’re still valid here as for many people they are side hustles. Plus, it was my first time starting ‘something’ outside of a job for someone else.

Aim: income

Status: closed

Why and how did I get into it?

This is a simple one – i loved the art of DJing. I studied a degree (economics, which I hated at the time) and upon graduating wanted to do something I loved. I casually gigged at the time, took it way more seriously when the alternative was a ‘real job’.

What was the business model?

As a DJ the model was simple – paid per gig. I was lucky enough to travel to pretty much every continent and for about 5 years be abroad for 3 weekends a month. The journey was incredible, the shit around it i’ll come on to shortly!


As a record label, revenue came in two main ways: sales and licensing. Revenue came from music sales, licensing from compilations and/or adverts (where a royalty fee was paid).

Pros and cons

The largest pro was easily the priceless experiences. Meeting incredible people, going to fantastic clubs and parties, and moments that money cannot buy. A club being shut down by military with guns and tanks, pausing mid interview on live TV in Thailand as got distracted by Wayne Rooney getting sent off for England in the World Cup, near death experience between clubs on Eastern European roads to mention but a few. 

In terms of financial reasons, DJs can earn A LOT of money per gig. Breaking into the top tiers you’ll need talent, luck and probably some success as a producer – but even in touring or regular gigs you can earn high 3-figures for a couple of hours. 

As for a record label, this is almost as hard as they come to make money. Don’t get into it for this reason!

The largest downside is ALL OF THE OTHER SH!T that goes with running a business. All I wanted to do was play music, give people moments and memories, just play amazing gigs to breathtaking venue to amazing clubbers. But… I’d spend a full time week doing other stuff to make sure the gigs were good enough and I was ready. Chasing promoters, coordinating flights, managing logistics, checking itineraries, promoting information, negotiating, chasing payment, accounting, partnerships… the list is endless. And 90% of it I hated. 

Knowing what I know now, I’d have leveraged the hell out of everything. But, this was before the gig economy, virtual assistants and a really connected world. Who knows, if I was 10 years later maybe I’d still be doing it! 

Biggest lesson

My first lesson was learning to not underestimate all of the stuff that goes with running a business. However, this isn’t the biggest lesson from this. The main one is something i’ve really taken with me in so many places and had a HUGE payoff in my life .

So here it is… be ahead of the trends. One thing that I feel lucky to have learnt at the relatively young age at the time is to follow trends and be ahead of the direction markets are moving. Needless to say, i learnt it the hard way. I was owed over £10,000 by my largest record distributor, one that went into administration. When they went into administration they almost took me down with them. Similarly I had 15k Twitter followers back in 2009 then closed the account as I didn’t see a practical use for it, whereas now having an engaged following socially is critical. 

I got burnt for not seeing what will happen.

So now, my default i’m looking 3, 5, 10 years into the future. I’ve learned to have patience on a longer time perspective and to start with where I think things will end up. I now just work out how to place myself on that trend to capitalize instead of being taken out.  

Bag hire company

Aim: cashflow

Status: closed

Why and how did I get into it?

Those in the US will be familiar with Bag, Borrow or Steal, yet in the UK there wasn’t a dominant player. In fact, I still don’t think there is a dominant player in the designer handbag hire/subscription space. The simple way of getting into this is that my wife likes LOVES expensive handbags. So, whilst building up a personal collection we thought of monetizing it. After all, most sat in a cupboard most of the time… although it could have easily just been an excuse to buy more!

What was the business model?

People pay a fee to hire a designer handbag. They either pay a one-off hire fee for a few days, a week, or have a monthly subscription in which they change bag each month.

Pros and cons

The biggest pro was making money from existing bags. The downside was scaling it required a lot of inventory ,which was capital intensive and expensive upfront. This leads perfectly into the biggest lesson.

Biggest lesson

One of the other challenges was the customer acquisition cost. Similar to Netflix, profitability comes when they ‘win’. Eg. when they reach a certain scale that they win in the market – they’re known, the cost of customer acquisition is minimal and barriers of entry are high due to this. Whilst gross margin on each order was fine within a smaller scale, it wasn’t huge. The subsequent impact of this when compounded with inventory costs meant the business didn’t scale as easily as hoped.

I still believe someone will do this successfully, it will just take time (and deep pockets with funding) to reach a large enough audience to make the pay-off worth the effort.

Chocolate fountain hire company

Aim: cashflow

Status: sold

Why and how did I get into it?

I hired a chocolate fountain for my wedding. Anyone that has done the same will be AMAZED at the cost. I did a quick bit of research and realised the costs were pretty insignificant to enter this market, compared to the charge out. I’ll cover this in the model below in more detail. The largest challenge seemed to be generating bookings, which being a marketer I didn’t think would be a challenge to do.

What was the business model?

Hiring of a chocolate foundation service for 2 hours was a fee of £250-400 depending on the number of guests. This would cost approximately £50-70 in consumables (things to dip and chocolate). So, you could easily have £200-300 per booking to cover staffing and travel. You can do it yourself or pay someone once you’ve trained them. 

A second hand chocolate fountain can be purchased for £500, which means your first 2 bookings should put you at breakeven. After that is profit.

Pros and cons

For me, a big pro of this was through the solid profit per booking and minimal cash outlay. Within a month this way you’re in profit. You could easily make £200 for 3 hours on a Saturday night (or £150 is you paid someone else to do it).

The biggest downside was that I hated the work. I had no passion in it (I don’t even like chocolate!) As such, it was too much of a distraction from everything else I had going on.

Biggest lesson

Don’t do stuff just for the money. It won’t last.

HMO management company

Aim: cashflow

Status: sold portfolio, retained company equity

Why and how did I get into it?

This started out of a personal need. I was investing in shared houses (also known as HMOs, Houses of Multiple Occupancy) and found that all agents i used to working with from a single let perspective didn’t know much about HMOs. They didn’t know how to advertise to guests wanting just a room, their systems weren’t effective in running them, they didn’t know the tenant types and market, nor were they clear on legislative and compliance requirements. So, I created a company to initially manage my own properties. This quickly scaled to support other local landlords wanting shared house management.

What was the business model?

The business model was simple at its core: get paid by a landlord to management their shared house. In effect, we ran this in two ways:

  • A fixed % on rental income.
  • Guaranteed Rent, fully managed model where we provided the landlord fixed rent and covered all bills, maintenance and running costs. You may have seen this model called rent-to-rent (R2R) if you’re in the property industry.

The latter was a far more intensive model, however the upside was greater margin due to the value delivered in the services. It effectively meant a landlord could be 100% hands-off. All they did was pay their mortgage each month, and get paid with effort or hassle from us. Or profit could be as high as 20-30% of the rental income in this model, whereas with a % model the maximum would be 12% of rental income. 

Pros and cons

Cash flow of this is a big upside, especially in a fully managed model. You have limited start-up costs and generate gross profit pretty much on day one. The big plus for me was that I needed the service anyway. I’d have been paying someone else to do the work, so by effectively paying a company of mine it wasn’t costing anything. Then, profit obviously grew as we grew the number of landlords we were working with.

Whilst not capital heavily initially, knowledge wise this was a big gap to fill. Compliance and legislation as a landlord is always changing, as a letting agent is changing and tenant rights are changing. Knowing what you can and can’t do is key, so took time to understand. Equally, knowing what types of tenants, appeal to what areas, and what types of houses and rooms is a learning curve. It is not the same as a single. You also have to factor in building the house dynamics as one bad tenant can end up costing a lot of money.

Additionally, most side hustles up until this point had been around marketing problems – eg. how to get leads or sell to people online. This was a different game altogether as was far more operational, system and process related. 

Biggest lesson

Systemise and outsource – way before you need to. I started this as letting agents couldn’t offer me the services I wanted. What I didn’t want to do is do that job for them!

Getting help is key. I don’t mind house viewing (looking for opportunities and deals, but I don’t like doing tenant viewings). Whilst my wife who was full-time in property did almost all of the viewing, she didn’t love them either! She likes building relationships with agents. Plus, we both hate admin. And, within property and lettings there is a tonne of it! 

So, we outsourced as much as possible:

  • Viewing scheduling
  • ID and credit checking
  • Check In and Check Out logistics
  • Repair and maintenance issues
  • Financial reconciliation
  • Chasing of payments
  • Tenant communication

Putting systems in place and a few hours each week of a Virtual Assistant (VA) that specialises in property handled all of the above for almost 50 units. It is probably a £100-200 monthly cost to mean you’re not working in the business and can look to grow it instead.

The other lesson here is timing. I got into this market at a good time. Grew nicely. But, could see the landscape changing and becoming far more competitive. With many other things I had going on, my energy and priority wasn’t to keep growing this. So, over a period of time scaled out profitably passing on agreements to other companies for many 4-figure fees.

Property management lead generation business

Aim: building wealth through property sourcing to invest in (but cash flow in the immediate term through deal packaging)

Status: active

Why and how did I get into it?

I wanted new inquiries to grow the HMO management business and my portfolio more quickly. So, in addition to working with local estate and letting agents, I sourced leads. I’d either use these personally to invest in, through the HMO management company, or sell them to other property companies.

What was the business model?

Sourcing leads from home owners wanting to sell or landlords wanting to rent their property. I would agree terms, then package these as leads or deals. These would be sold to companies that could help fulfil their needs. I source these through many methods, including: online marketing, leaflets, letters and even knocking on doors!

Pros and cons

I told you that somewhere in the side hustles they start to become logical 😉

This is mainly through adding complementary streams to activity I was doing (or knew). I know I can generate leads online and through marketing – I’ve done it for many many companies. Afterall, i’m on the board of an award winning marketing agency. I know what property investors look for, as I am one. And I know the local property markets well, as I invest there.

So given those 3 things; the is just a combination of them. Perfect.

The biggest downside was focus. This is yet another thing, to start, build, systemise and constantly dip into.

Biggest lesson

Getting back to basics and street level tactics. Ugly marketing – not just online digital stuff. In their face messaging that is direct; stuff in shop windows, letters, leaflets, boards – putting leg work in. And above all, take consistent action over an extended period of time. You need to build up momentum.

Investment affiliate site

Aim: cashflow (potentially sell once asset has enough value)

Status: active

Why and how did I get into it?

I’ve always been active in investment markets. You can ready about what I invest in and why here. In talking through options with my wife, there were a few areas she wanted to understand more. Yet, when researching online the information as aimed at men, by monotone men. She struggled to get educated in the subject areas due to the lack of appropriate and engaging information available for her. So, Nat being awesome and being her, she wanted to do something about it. So, in effect this is more her thing – I just support with marketing. However, the monetisation online is also purely in my court. 

What was the business model?

At this stage, it is a simple affiliate site. Nothing fancy. Get an affiliate (or referral fee) when someone buys a product from a link on the website. Future options include training and membership groups, but these are some way off until the engaged audience grows.

Pros and cons

Another hustle requiring investment upfront of time and money, with a long tail of return. So, early months are a net loss. We’re also entering into a very competitive space around investment, trading and finance. Monetisation and fees can be fantastic, however, generating traffic is extremely challenging on a new domain.

The future upside will be an asset that generates income with little on-going effort. Even now, time invested is minimal as the content strategy is largely fuelled by questions women wanting to invest ask – with all writing outsourced.

Biggest lesson

Patience. Having spent most of my time marketing for large brands, it is easy to overlook how much equity they have built up. 

  • Brand equity which helps conversion rates and engagement, 
  • Market awareness which means you organically just get inquiries, 
  • Domain authority which means SEO returns positive results quickly, 
  • Large social followings which means that reach is naturally large
  • Large customer base which means word of mouth scales impact

When starting from scratch – a new website, new domain, new site all takes time. You have zero reputation, trust or equity. 

This means that for results to build up with search engines and target audiences, takes time. Be prepared to invest this, not just intensively upfront, but over an extended period of time. Anyone says anything different is not being fair. 

Business lead generation site

Aim: cashflow (and proof of concept for a future venture)

Status: active

Why and how did I get into it?

In having many conversations with small business owners it wasn’t difficult to notice that they all struggled with where the next deal, win or order was coming from. They were constantly chasing new business and many lacked the skills to do this at scale, efficiently online. Given my previous business and professional experience I knew I could help them.

What was the business model?

Simple. I generate leads for their business. They buy them off of me for an agreed cost per lead. This could be through numerous mechanisms including SEO, 3rd party websites, paid media and social channels.

Pros and cons

I’m not going to lie, I thought this would be way easier than it was. I massively understated the effects of momentum and level of effort to get traction. As a result, payback has been slow and i’ve deprioritised this. It is still active, but pretty passive in developing due to my focus. As a result, progress is small and incremental. 

Biggest lesson

Similar to some of the other lessons is around focus. Whilst this take limited time (and money) of mine, the drawback is around effort and mental bandwidth. I’m not actively involved enough to make an impact in moving it forward and without getting enough critical mass it isn’t (and may not) become self sustaining.

Marketing software – asset building side hustle (active)

Aim: building a business

Status: active

Why and how did I get into it?

In working at Ledger Bennett, I worked alongside a couple of the founders of another company specialising in Marketing Technology services. We noticed a gap in the market for a software product and I was invited to buy-in to the company as a partner given my differing skill set and experience around go-to-market strategy and scaling growth through marketing.

What was the business model?

We sell Software-as-a-Service (SaaS) to enterprise company that helps with web form management. The model includes an upfront implementation cost followed by annual recurring revenue.

Pros and cons

Being a self funded scale-up we haven’t had outside investment to date. This has had both pros and cons. Pros that we have been able to heavily focus on product fit and development without aggressive growth targets. The cons being that progress in places has been slower in areas than desired through having to prioritise investment decisions. One of the big cons here in working in an agile format, iterating with view on building a best-in-class product.

Serviced Accommodation – cashflow side hustle (active)

Aim: building a scalable business

Status: active

Why and how did I get into it?

Changing taxation and local rental market meant I was receiving reduced cash flow from my portfolio. So, to increase this I was looking at alternative models to increase my cash flow. I knew HMO wouldn’t work in the markets I was in through past experience, so serviced accommodation was the most suitable route.

What was the business model?

Renting properties out on a nightly basis as opposed to monthly rates on long term (AST contracts). I operate this on both rent to serviced accommodation (R2SA) and on properties I own. You do have increased overheads and risk with this, however have a far higher upside than on a traditional single let.

Pros and cons

This isn’t property investing. It isn’t passive. You’re in the hospitality game. The upfront learning curve and implementation is also extremely steep: processes, systems, OTA, commission rates, terms & conditions, pricing strategy, marketing, listing management and optimization just to name a few things! Once in place, lots of the running can be systemised and automated. However, it still isn’t low touch like a single let.

The pros are cash flow. From a modest investment per property (especially on R2SA) you can get full payback in 6 months and then into on-going profit. 

Biggest lesson

Get educated and don’t go too quickly. As I said before this isn’t a typical property business. There are so many more aspects that need to be understood to operate successful. I wanted to go fast and realised very very quickly into the journey the need for systems and support from specialists in the right place.

Your lessons?

I’ve shared my journey and lessons on side hustles, what are yours? I’d love to hear what challenges, lessons and successes you’ve had!?