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Bootstrap Fireside Chats, Part Two – Nick Telson, Co-Founder, Design My Night

In the second part of our interview with DesignMyNight Founder Nick Telson, we dig into the lessons he’s learned from his years as an entrepreneur.

From specific actions that any entrepreneur can take to get an idea off the ground for free, to some sage closing advice for founders wanting to follow in his footsteps, this second instalment is packed full of insight, candid reflections and even a shout out for his new venture trumpet.

It’s a conversation that offers you tangible tools that can be used, today, to pursue your own venture ambitions.

Looking back, are you happy you chose to build this way, and why?

Yes, we are happy that we bootstrapped. At the time we did it because we didn’t know any better, rather than it being a conscious decision, but it forced us to focus. We were in our mid-twenties and if we got the money we have raised with Trumpet we would have spent it poorly. 

Bootstrapping forces you to appreciate the value and importance of money. For example, it makes your hires more important. If you’re spending thousands on recruiters hiring people who do not work out then you’re losing cash you can’t afford to waste. When it came to hiring at DMN, we did so based on personality not just skill. You can train skills like sales, customer success and customer support but you can’t train the right attitude. In our case, it meant we built a super young team which is also all we could afford at the time! 

When we exited, most of our managers were young people who understood DMN and how we wanted the business to operate.

We had our hands on levers of what makes a business successful right from the start. Bootstrapping forced us into great habits that set us up to be responsible business owners.

If you were speaking with a potential founder who thinks bootstrapping is not an option for them, what would you say and what are the first steps?

Bootstrapping is not an option for everyone. You’ve got to come from a place of slight privilege to be able to bootstrap. You still have to buy some tools to get going, and some founders literally have no money to spend, and might have a child to support and bills to pay at the same time. 

But even in that situation, you can look at what functions require the investment of time, not money. Take market research, gaining feedback on your idea and speaking to customers costs nothing, but it’s so important. Doing that well could get you to revenue faster. You’ve always got to be thinking, what is the quickest way to get cash into the door, and often that can be free. 

Think strategically, think what you can do, not what you can’t. You can outreach customers for free, set up a Typeform account, set up a Canva site for free.

There are no code tools like Bubble which require no development experience to use, you can use this to build an MVP of your product. With the speed AI is developing, you might not need agencies to do content marketing and SEO strategies. You don’t need thousands of pounds in your early years, there are lots of ways that you can be clever. It’s a mindset. Google free ways to start businesses and go from there.

Can you tell us about Trumpet?

We’ve gone a totally different mould with this venture to DMN. 

We’re now in a different position in life. We don’t have to work but we are too young not too, so any business we start now must have global potential, be product-led and instantly scalable.

We had lots of ideas before settling on this one, six or seven during covid, when we landed on Trumpet. First, we took the same steps as with DMN, speaking to over 100 salespeople and founders about the idea, and it seemed to resonate with the people we spoke to. 

We are trying to modernise and digitise the sales process, more specifically everything that sits between the outreach phase and closing a sale. In B2B sales, it takes an average of 80 emails to get a deal done. That’s not an efficient way to do business! So, with Trumpet, we’ve come up with the idea of creating personalised micro-sites (Pods), that allow you to streamline the clunky process of closing a deal, by navigating through each stage in one place.

We’ve created a no code tool where a salesperson can spin up a personalised microsite in 30 seconds where you can host video and audio content, links, use cases, mutual action plans and more; a microsite that you can use to get a deal done in one place, with all the resources at your disposal.

What learnings have you taken to Trumpet from your previous experience?

This one is tough to answer. It’s less the big thematic issues, and more the daily strategic decisions that are the ones where we can think back to DMN and remember how a certain approach or decision worked out. We’re targeting a different market and customer, we’re global and VC backed, so we are again learning new things which is great but there are a lot of day-to-day operations and processes that we’ve learned from previous experience. That comes from the bootstrap mentality.

Is there something we haven’t asked you which we should, or any final advice you’d like to offer those who are deciding to make the leap?

One final piece of advice I’ll give which might come across as negative but is not intended to be, is that being a founder is not for everyone.

You can have the drive and passion to work in startups as an employee, it does not have to be as a founder. If you love the startup world, go find start ups that have raised a seed or pre seed investment round, be an early-stage employee at a company and you can still get the real experience, you can learn, you can listen, you should get share options so don’t just jump headfirst into being a founder. 

Starting a business is all encompassing, 24/7, the reality is the old school hustle culture to get it going is crucial. You won’t take a salary in the main, you’ve got to be sure that you can survive. One big reason for failure is the founder runs out of personal cash. You’ve got to think, can I survive for 9 months without a salary. You’ve got to make sure the loved ones, family and friends are fully on board with what you are doing. You are going be absent. You’ve really got to get your ducks in a row, and think, am I mentally strong enough to take on 24/7 non-stop pressure, and essentially become addicted to something.

If not, that’s fine. Go work in a startup and get the buzz of start-up life that way.