• Lauren Leopold

12 tips for growing a successful side hustle while holding down a 9-5

Updated: Feb 18

Ever seen a small business with a fab idea and wondered how it got off the ground? Read on to find out how a simple observation about the drab colour of people’s running shorts grew into a successful side hustle for this exercise-mad couple from Essex, plus their top tips for success.

Meet my ex-client Sam Goldring. By day she runs the social media team at Barclays UK, creating brand campaigns across Facebook, LinkedIn, Pinterest, Twitter & Snapchat. Her evenings and weekends are spent running (no pun intended) Happystride .


She says: “We (my husband Pete and I) both believe that running can make you happy, so we decided to create a business selling bright running shorts that supports mental health - our shorts are bright and happy! We get feedback that this is really key for our customers - that the brands they buy from align with their own values too - and we know that it encourages them to keep coming back”.


How the idea came about

Unlike some side hustles that were borne out of the founder wanting to leave their corporate job, Sam’s experience has been quite the opposite. She says: “I love my job at Barclays. It's really varied and fun and the fact that I’ve been there 8 years shows how much I enjoy it. Pete and I had always talked about setting a business up together one day and we’re both into motivational books. Pete read ‘Shoe Dog’ about the guy who started Nike and got really inspired by it. He’s obsessed with running, having run over 50 marathons and came back from a Park Run one day having noticed that everyone was wearing plain black shorts. He said it was a bit of a shame that bright running shorts aren't a thing and that’s when the idea for Happystride was born!”


They started with just 2 pairs of shorts in their range, but now have over 12 pairs of shorts (and increasing all the time), have moved into selling leggings and are now branching out into socks as well. What started as a passion project has now grown into a fully fledged business, but they don’t take their success for granted.

“It was so exciting hearing that ‘Ding’ sound from Shopify telling us we’d made our first sale and we still get just as excited to this day. We absolutely love every sale and wonder who it's for and how they found us. Even as the company grows, that excitement will never go away, just like the first day. It's so satisfying seeing the actual products after going through the whole design process, seeing the fabric and then the final products. It makes us realise that this is possible - we had no clue what to do when we started it. We’d never worked in making clothing, we just had a passion for running, knew what we were good at and knew there was a gap in the market”.

Their 12 top tips for success:


1. Start small and test your idea

We started off with 2 designs - the parrots and the bananas - to keep it quite simple test our idea. We ordered 50 pairs and said that if we sold them within a month, then we’d order some more. To be honest we hadn't done much research or told too many people about it, so when we launched on Instagram, it was just our friends liking us! But we had such a great response (one person even bought 10 pairs in one go to give to family & friends!) that we ended up ordering 50 more pairs. Once we’d sold 100 pairs we knew there must be something in it.


2. Outsource the things you can’t do

It can be tempting in the beginning to try and do everything yourself, especially if you’re trying to save money. But Sam and Pete are proof that if you’re willing to invest some money in getting experts to help you, you can get your business off the ground a lot quicker and free yourself up to work on the stuff you’re really good at. “We may both be creative but we’re not clothes designers, so we quickly realised we’d need to bring in experts to help us. We worked with Upwork.com who put us in touch with the designer and we’ve worked with her ever since. We also knew we needed a shop front and needed help with eCommerce, so we got set up on Shopify, which does it all for you.


3. Get clear on your USP and develop your brand

My mantra is always to just get started and don’t let things like branding and logos hold you back. That’s all well and good in the service industry, but for product related business it’s more important in the beginning. Sam says: ‘We don’t suffer from imposter syndrome as we’ve been really tough on ourselves to make sure we have a solid USP, ie how we’re different to other brands out there. My background in marketing, plus a great book I read called ‘The Purple Cow’ by Seth Godin talks about making sure that your brand is remarkable, really helped. In terms of branding, we obviously wanted happiness to come through in everything we did, which is where the bright colours come in, plus our idea of supporting mental health charities with every sale.


4. Combine your passion with what you're good at and you’ll never work a day in your life

Sure, we can all come up with tons of ideas to try out as a business, but the sweet spot is always passion and skill. Sam says: “The reason Happystride works is that Pete's so passionate about running and I'm passionate about - and skilled in - the branding and social media side. If you choose something you're passionate about and that excites you, you don't think of it as work. Pete’s so passionate about running, so he doesn't even see it as a job, he’s just so excited to get on with everything. That's why it's so important to choose something that you're passionate about.


5. Utilise your 9-5

Sometimes we can become so focused on our side hustles and disillusioned with our 9-5s that we forget all the valuable skills it has taught us or can potentially teach us. What training courses can you go on? What skills can you utilise? Sam says: “My job has come in really handy - we’re obviously using smaller budgets than I have at work, meaning we've had to take a very different approach, but the theory has really helped.”


6. Don't put too much pressure on yourself and have fun!

It can be tempting at the start to grow quickly and make the business a ‘success’, but Sam’s advice is to ease up on yourself and take it slow. “Because it's a side hustle we haven't put too much pressure on ourselves, like we might do if we were working in a big corporate business. We have set ourselves targets around the number of sales, etc, but because it's something on the side of our 9-5s and we’re not desperate for it to work, we haven't put pressure on. It obviously was a risk though - we both put some of our own money in to set up the business, but we believed in the concept and it’s paid off.


7. Listen to your customers & get feedback

Feedback from your customers can be priceless, regardless of whether it's positive or negative. It all helps to evolve and improve your business, as Sam and Pete have discovered: “We’re always looking at new ways we can serve our community - the leggings idea actually came from a customer suggestion on our social media posts. That’s one of the great things about social media is you get constant feedback - dont take it personally, use it to constantly innovate. Get your minimum viable product out to market quickly, test, get feedback and learn and evolve over time.


8. Utilise down time around your 9-5

Side hustling can be overwhelming, especially when trying to fit it in on top of your 9-5. Sam recommends working out what needs to be done when and finding spare time where you can. “In terms of time management, my involvement in much more of a weekend job. So when we were commuting, I might be creating posts or something, but it never seeps into my day job luckily as I’m far too busy at Barclays to even think about Happystride during the day. Luckily there’s two of us and we can manage it all in the evenings and at the weekend. It just works”.


9. Be optimistic and make the most of every opportunity

When terrible things happen, it’s easy to just see the negative impacts on our life and business. But Sam recommends always looking for the opportunity in everything. “Obviously COVID has been awful for so many people from both a health and business perspective and no one knew how it was going to impact them. We were fortunate though, that our industry was one that picked up during the first lockdown and we saw it as an opportunity. It actually encouraged us to make more designs. and increase the product line to get more reorders. We also did a few press releases about how people were getting out running in difficult times and that we were helping them to do that. That got us coverage in the local press and Womens Running, which was amazing. You have to take the opportunities as they come and really go for it, even if you’re not sure what's going to happen.”


10. Learn and develop as you go

You can’t expect to know everything at the start or get everything right the first time. Sam & Pete have learned a lot on the job and have drawn inspiration from self development tools like books and podcasts. She says “I was listening to one about another clothing brand and they got into trouble with their name being similar to another famous brand, which inspired us to get Happystride trademarked. Other things that have inspired us are ‘Post Coronavirus’ by Scott Galloway and the ‘How I built this’ podcast by Guy Raz, which is all about how now famous brands started out, Sam says they are really worth listening to! “It’s amazing and inspiring to see from these books and podcasts how successful brands such as Gymshark have succeeded in such a short timeframe with their founder Ben Francis now worth over £1billion!!


11. Reach out to influencers - don’t be scared!

A lot of what goes into being an entrepreneur is having the confidence to try things even if you feel like they may not work. As Sam says: “Influencers have been really useful to us, but it’s all come down to having the confidence to ask - the worst that can happen is you can just get ignored. We’ve reached out to loads of magazines and influencers - the fact that you can just DM someone on Instagram and ask ‘Can send you a pair of shorts?’ is nuts. We obviously don't have a budget to pay influencers, but the amount of people who’ve replied to us is amazing and they really want to support small businesses. We’ve seen sales off the back of Suzanne from Hearsay and also Anna McNuff - when Anna did her post,we sold 20 pairs in the next hour which was just AMAZING!! If we hadn't messaged them, we wouldn't have got those sales. I would say, don't worry about giving away free products and services, just work out how much it would cost you in paid media - it's always worth it.


12. Start with organic social media, then test and learn with your advertising

Social media is now a key promotional channel for most small businesses and Happystride is no exception. Sure Sam has a ton of knowledge from her job at Barclays, but she still recommends adopting a test and learn approach, whatever your level of expertise: “It’s all still a learning curve, but my tips would be:

  • Start off with organic or ‘free’ social media and get friends and family to follow, reshare posts etc.

  • We got a lot of organic growth from influencers posting, but we also include an insert every time we send shorts out to encourage people to post about them.

  • We also know the running community searches for hashtags, so a key part of our strategy is constantly researching new ones.

  • We also follow running instagrammers and to get them to follow us back.

  • When we run paid ads, we test copy and image variations to see what works, eg a product on its own vs a person wearing a product.

  • Also, plan everything ‘IG first’, so if we’re taking a photo we plan it for Instagram even before our website!

So what have been Happystride’s biggest achievements and what does the future hold for them?


Sam and Pete have already had some amazing achievements such as getting stocked by two local running shops and becoming famous within their hometown in Essex. “It’s such a buzz seeing our shorts hanging up in the shops and seeing people running around in them! In lockdown, a lot of people took up running and had a bit more disposable income, so we saw quite a few new customers testing our products and seeing someone running past wearing a pair of parrot shorts is so special! And because they're so bright, they seem to sell themselves”


In terms of the future, the couple is optimistic but realistic: “It's not big enough to give up our jobs at the moment - but who knows what will happen in future! The stage we’re at right now is about building the brand, we know we need to advertise and continue building our following. The ultimate goal for us is people seeing a runner wearing a bright pair of shorts and assuming its Happystride - being the first brand that comes to mind when they think about running gear. Look out for new launches coming very soon!”.


Do you dream of starting up a side hustle like Sam and Pete have? Or maybe you already run a business and want to take it to the next level. Either way, book in a free discovery call to see if we vibe!

Meet Lauren


Career Change & Business Coach and Side Hustle Queen


Hi, I'm Lauren. I burnt out, hit rock bottom and used the experience to manifest my dream life. I now help passionate and ambitious women change career, start side hustles and grow businesses. I'm living proof that you can - and deserve to - have it all.


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