Nick Telson

Founder DesignMyNight (Acquired '19) 🍹 | Co-Founder trumpet 🎺 | Investor in 55+ Startups (Currently not investing in new deals) 😇 | Podcaster 🎙️| 🏳️‍🌈

Hey!

I’m a London entrepreneur, currently living in Boston.  Also an angel investor, podcaster, startup mentor and public speaker, whose speciality lies in talking no-nonsense founder/investor advice and help. I'm currently co-founder of new B2B sales tool, trumpet, host of Pitch Deck podcast and co-founder of an angel investing venture-arm, Horseplay Ventures

I previously co-founded DesignMyNight, back in 2010 and managed to grow that over 7 years with minimal angel funding, to 100+ employees, 15,000 SaaS customers and 8m monthly uniques on the website. We exited to Access Group in 2017.

I live for the early stages of startups - building the brand, finding product market fit, iterating quickly and building out a team. Most of my content is centred around this, as well as tips from an angel investor. Even after exiting to financial freedom, I caught the founder bug again and have co-founded my next startup, trumpet, in 2022; looking to disrupt B2B sales and kill the sales pdf deck. Follow me on here while we build out this new journey in public.

Please feel free to ask for any advice or help, whether a founder, startup employee or investor and I will always endeavour to do what I can. I'm also a regular guest on podcasts, startup speaking gigs and webinars, so feel free to reach out to me if you are looking for guests/speakers. 

I do respectfully ask not to be pitched for investment in my Linkedin DMs and instead go through Horseplay Ventures. Hopefully my podcast is also a treasure trove of information for those looking to raise early-stage investment, thinking about it or just interested in it - search for Pitch Deck by Nick Telson.

Co-Founder

Nick Telson-Sillett

Big news at team trumpet 🎺as we finally say what all our customers already know and move into our next era.

We are way more than just a digital sales room. It's a feature now, not the product.

While our DSR remains #1 globally and will continue to be so, we felt it was time to create a new category.

🎺 Rory Sadler explains it best in the short video....

Over the last 40 years we have seen sales tech change from CRM to Sales Enablement to Rev Enablement to Rev Intelligence and we now have a tonne of siloed products...

Trumpet's next chapter aims to combine all of these into one AI-powered workspace where Enablement, Collaboration and Intelligence all work together.

We are the Intelligent Go-To-Market Layer for Revenue Teams 

...combining CMS, Sales Rooms, Workspaces, Collaboration (internal and external), Org Charts, Proposals/Quotes, Buyer Engagement Intelligence, Actionable Intelligence, Coaching, 10+ other AI features plus 55+ integrations....

One connected, collaborative and intelligent tool.

Over to you Rory....👇

Co-Founder trumpet 🎺 | Founder DesignMyNight (Acquired '19) 🍹 | Investor in 55+ Startups 🤑 🏳️‍🌈

Being a second time founder is wild.
You are still guessing, but you know exactly which guesses nearly killed you last time.

With DesignMyNight I learned plenty the hard way.
This time round with trumpet 🎺 I have been very deliberate about changing some of my defaults.

Here are the 5 biggest changes I have made.

1) I designed the business model before the product

First time I was obsessed with the product idea. The model was an afterthought. Now I start with ACV, margin, sales cycle, who actually pays and how often. If the numbers did not work on a simple spreadsheet, I do not build it.

2) I am ruthless on people quality, not people quantity

First time I hired for relief. Too busy, drowning, just get someone in.
Now we hire very slowly with scary high bars. One great operator beats three people we need to manage every day. 

3) We optimised for distribution from day one

Before, product was the obsession and distribution was an afterthought.
We built, then hoped. Now we only build things I already know how to sell. Audience, channels, partnerships, content. If I could not see the path to customers, we did not build it

4) I was far more intentional with investors

First time I was just happy anyone said yes. Wrong. This time we reference checked investors harder than they reference checked us. Values, speed, how they behave when things dip etc. Money is a commodity, behaviour is not.

5) We run the company on a clear operating rhythm

Last time it was vibes and firefighting. Some weeks we were busy but not actually moving. Now we have monthly metrics, clear priorities, operating playbooks and clear owners for each area. t is a lot harder for the business to drift without anyone noticing.

Second chances are rare.

The trick is always be learning and not wasting the pain from the first

At trumpet 🎺 we recently told a big paying customer no.
To a chunky custom build that would have made us hit Q1 quota already.

On the surface it looked perfect
Huge logo
Excited champion
Budget approved

But here is what actually went on behind the scenes as there are learnings for all I think...

- The request would have dragged us off our ICP
- The use case was cool but miles away from our core users
- It would have pushed trumpet toward being an agency not SaaS
- The feature did not compound
- No clear path to reuse across our base
- No way it made the core product better for everyone

Sales loved it for the wrong reason
 
It made the deal bigger
But it would have slowed us down

❌ High implementation cost
❌ High support cost
❌ Low reusability
 
So we told them no
Respectfully
Explained why
Offered a trimmed version that kept us closer to our main product and kept them happy

We did lose some short term revenue

But we kept something more important

A product that gets better for most of our customers and keeps us bang-on focus across the board

From the outside it is easy to assume growth comes from every yes

At our stage it can also come from choosing the right no.

We just crossed 1000 reviews on G2. F**k yeh! 🥳
And we are still sitting at number 1 in our category globally

I am proud of that
But I'm even prouder of how we got there

Every single review is treated like a product slack message from our team
• The glowing ones show us what not to break
• The brutal ones show us what to fix next
• The detailed ones end up as product specs

We read them ALL
We tag them
We turn them into roadmap decisions and UX changes

This is not a vanity metric for us
It is a feedback engine

So THANK YOU to every customer who took time out of a very busy day to write one line or ten paragraphs about us

You helped us get to 1000 reviews
You will be the reason we earn the next 1000

Relentlessly customer centric is not a tagline for us
It is one of our trumpet values and we stick to it religiously.

Having observed over 50 founders that I've invested in. Here is a list of 50 characteristics I think make a good founder:

1) Obsession with the problem
2) Ability to hear no ten times and not take it personally.
3) Writing things down clearly
4) Knowing when a tiny ugly experiment is better than a beautiful strategy
5) Hiring people because they are better than you
6) Firing fast when your gut has already decided
7) Saying I do not know without flinching.
8) Caring more about cash in the bank
9) Being honest in investor meetings
10) Being able to sell
11) Protecting deep work time
12) Admitting when the market does not care about your idea
13) Treating customer complaints as free consulting
14) Knowing the difference between a bad week and a broken business.
15) Letting your team ship work that is not perfect
16) Making clear quick decisions in meetings
17) Staying calm when numbers are bad
18) Being able to explain what you do to a kid or parents
19) Choosing boring consistent progress over heroic all nighters
20) Talking about money openly
21) Saying no to cool opportunities that do not move the core metric
22) Giving credit to the team in public and feedback in private.
23) Knowing when your own ego is the real blocker
24) Treating investors like partners not parents.
25) Keeping your personal burn rate low
26) Asking your best people what they really want and actually listening
27) Being willing to walk away from mis-aligned money
28) Staying curious about competitors instead of obsessed
29) Realising culture is set by your actions not what you simply write down
30) Checking the numbers yourself
31) Becoming less important to daily operations as the company grows
32) Being honest when someone great has simply outgrown the roles you have
33) Keeping a small circle of people who will tell you when you are being an idiot
34) Turning complex plans into one simple next moves
35) Not confusing being busy with making progress
36) Knowing which metrics actually matter at your stage
37) Staying kind when you are stressed
38) Being able to pitch with the same energy at all times
39) Choosing long term trust over short term wins in every deal
40) Protecting your sleep
41) Not needing to pretend things are amazing when they are not
42) Giving your team context instead of random orders
43) Letting go of old decisions when new information arrives
44) Knowing when you are not running toward a clear goal
45) Saying I messed that up so the team feels safe to own their mistakes too
46) Caring about the lives your team beyond their output
47) Choosing a simple product/feature that actually ships
48) Being willing to be misunderstood for a while when you take a non obvious bet
49) Designing your work around your energy
50) Wanting the company to win more than you want to be the hero of the story

Which do you nail? 
Which could you improve on? 
What's missing?

Planning a year as a founder is not about a big strategy offsite and a shiny Notion page.

It is about a few hard decisions you are willing to live with for twelve months.

Here is how I now plan my year.

1) Start with the uncomfortable question - What has to be true in twelve months for this year to have been a success?
- Revenue
- Team
- Product
- Your own life

Write the answers in one sentence each. If it does not fit in one sentence you aren't getting to the core

2) Pick 3-5 non negotiable company priorities/themes

Not ten. 
Every project must map to one of the three. If it does not, it dies.
This is how you protect your team from chaos and yourself from distraction.

3) Turn priorities into bets not tasks
Instead of writing "Launch new pricing"
Write "Double expansion revenue by testing three pricing models by June"

Good bets have a clear outcome, a deadline, an owner, and a maximum spend.

4) Build a stop doing list
- Which customers will you stop serving
- Which features will you stop maintaining
- Which meetings will you cancel

Good strategy is also choosing what you will ignore.

5) Decide your personal rules up front
- Maximum hours you want to work
- Non negotiable time with family or health
- What you will say no to even if your ego wants to say yes

If you burn out the plan does not matter.

Your strategy is not what you write in January
It is what you refuse to compromise on in November

Having exited a company after a decade building, there is something about the exit planning I wish I was told earlier.

Your real exit plan is not a number
It is your life

We obsess over valuation, equity, secondaries etc but it hides a simple question - What do you actually want your life to look like before and after any exit?

For a long time my own plan was basically...
Work as hard as possible
Build something big
Sell
Life will somehow sort itself out

We design all aspects of our business and products in detail but treat our own life like an afterthought slide at the end of the deck

What did I want after an exit? What did I want my life to actually look like? What would I need to make this happen?

The shift for me was treating life design as seriously as a startup strategy
Very practical things

- Energy map
 When in the day do you feel good
 Do you want long deep work blocks or variety
 Could your role reflect that

- Relationship map
 Who are the people that truly matter
 Who gives you energy and doesn't drain it
 With who do I get genuine enjoyment with
 Who do I learn from

- Work map
 What parts of the game do you still love
 Selling, coaching, product, content
 Can your next chapter be mostly that, instead of owning everything again

- Money map
 What does enough actually mean for you
 Not for the tech press
 For you
 What would financial freedom look like?
 If you wrote that number down, you would probably act differently

Life design is not a fluffy vision board
It is a set of constraints you choose on purpose

If you're lucky enough to be ready to build for a second time, make sure you stop and think what you REALLY want out of it this time around.

You get plenty shots at building companies but only one shot at life 🤷

Building a startup is loud
But what if you're an introverted founder?

I am not the loudest person in the room
Never have been

For a while I thought that meant I was not the type of personality to be a founder

So I did what most introvert leaning founders do
Forced the big energy
Over prepared every social situation
Came home absolutely wiped

Over time I realised I did not need to become more extrovert

I needed to design the company around how I actually work best

Here is what that looked like in practice:

- One to one as the default
 Big networking events or founder events drain me
 So I stopped going 
 I would message people 1 on 1
 Have one good conversation
 Fewer people
 Better relationships
 More deals
 Less acting

- Writing as a superpower
 Extroverts often win in the room
 Introverts often win in the follow up
 I leaned hard into clear written updates for investors
 Thoughtful emails to partners
 Long form documents for the team instead of endless meetings
 It gave me time to think
 And it made decision making cleaner

- Designing my calendar like a battery
 Back to back calls all day
 No chance
 I started blocking recovery time after anything high stimulus
 No other meetings straight after
 Even thirty minutes to reset made me far better in the next conversation
 Leaned into async collaboration - emails and looms instead of meetings

- Hiring my social opposite
 Instead of worrying that I was not the big energy founder
 I hired people who were
 Commercial leaders who loved being out there
 Co-founders who enjoyed the spotlight
 Team leads who could shine without needing me all the time
 Their natural state was my unnatural state
 The mix worked


None of this means introverts get a free pass on the hard stuff

You still need to sell
You still need to pitch
You still need to have tough conversations

The difference is you can choose the format and the rhythm that suits you instead of copying the loudest founder you know

Some of the best companies I have seen were built by founders who do not dominate the room

They listen longer
They think deeper
They pick their moments

You do not have to change your personality to build a big company

You just have to stop building a company that constantly fights it.

And the band keeps growing 🎺

Following stronggggg recent growth in the States, we’re building trumpet’s Customer Success presence een further and looking for someone who wants real ownership from day one.

You’ll own your own book of customers end to end.
Onboarding. Adoption. Renewals. Expansion. Advocacy.

You’ll work closely with Russell Mitchell - Head of Customer Success, Alison Prator - Founding US CSM and the wider GTM team to help customers get real, measurable outcomes from trumpet and to help us build the CS playbooks we’ll scale with.

You’ll love this role if you:

• Care deeply about customer outcomes, not just activity
• Enjoy commercial conversations and helping customers grow
• Want to help establish a startup’s presence in the US
• Thrive in fast-moving, high-ownership, chaotic environments

This is not a feet-up on the desk role answering support questions that come in! If you want the easy-life this job isn't for you.

If you want real influence over how we serve customers, how we retain and expand accounts, and what Customer Success looks at trumpet as we scale, then this is for you.

If that sounds like you apply here 👉 https://lnkd.in/eim5uFBS

Paul Fairbrother

The Fairbrother Agency

I provide social media advertising services for high growth companies looking to scale their leads, sales, revenue and engagement using paid social.

Business Owner

Hootsuite

Senior Ads Specialist - Contractor

At Hootsuite I was a senior strategist providing social media advertising services to Hootsuite Ads and Hootsuite Social Advertising customers. Services included one to one strategy sessions, tactical reviews of ad campaigns, account audits and customer webinars. Key advertising channels included Instagram, Facebook and LinkedIn, although the wider digital marketing funnel was also considered. 

I was part of the team that implemented the rollout of Hootsuite Ads when the ad platform was acquired from AdEspresso and later helped customers transition from Hootsuite Ads to the newer Hootsuite Social Advertising platform. 

Clients were mainly Enterprise level and included healthcare, utilities, education and ecommerce but all industries and regions were covered. 

As well as assisting with the launch and ongoing strategy advice for ad platforms, I was also one of the founding coaches for Hootsuite Premier Services and created a range of training topics for social advertising that could be booked by any Hootsuite customer.

Senior Ads Specialist

AdEspresso

At AdEspresso we were aware that providing world class software for Facebook, Instagram and Google advertising was only part of the picture, customers also needed training and education on how to use the software and how to implement successful digital marketing strategies. 

To this end I headed up the Education team responsible for AdEspresso University. These resources included:

- community manager for the customer only Facebook group with over 7,000 members

- running a live monthly webinar and presenting a topic or booking a guest speaker

- writing and recording free video courses on how to use AdEspresso and how to succeed with Facebook & Instagram advertising

- delivering live paid for sessions on advanced Facebook & Instagram advertising strategies. This course generated over $80k in revenue. 

- conducting a monthly "$1,000 Experiment" and then delivering a blog post on the findings. This involved spending $1,000 on actual ads to see what's really working now, which gives far better insights than just theoretical ideas. 

- hosting regular Office Hours sessions, these 20 minute live videos gave a hot take on what's working now and involved interviewing both AdEspresso staff and guest contributors. 

- writing dozens of blog posts on advanced Facebook and Instagram strategy.

Head Of Education

I joined AdEspresso when it was a small team of just 20 people so got to have a lot of input on building up the Services side of the business, and then rapidly scaling up the Services after the company got acquired by Hootsuite. 

In my role as an Ads Specialist I delivered services directly to customers to help them succeed with paid social. Key services included:

- a managed ads service, similar to an agency where campaigns were booked and managed on behalf of the client. A range of industries were covered with a focus on ecommerce and lead generation. 

- delivering over 1,000 campaign reviews. These were 10 minute videos reviewing the ad campaign provided by the client, with the focus being on ensuring tactics were executed correctly. 

- hosting several hundred one to one strategy sessions. These "power hours" consisted of strategy sessions with the client where I would help them with their social advertising strategy, plus demonstrating how to implement that strategy in the ad platforms. 

Clients were across and range of industries and locations but with a focus on SMBs and mid market, as Enterprise level companies were covered by the Hootsuite side of my role rather than via AdEspresso.

Social Advertising Specialist

Shakeaway Worldwide Limited

As the manager for social media for all locations worldwide, I oversaw 50+ Facebook pages, 10+ Twitter profiles and 10+ Instagram accounts. Achievements included:

- creating a proper admin structure for the 70+ accounts to improve security and ensure all staff and franchisees had proper training on how to succeed with social media

- promotional launches for new stores

- running paid ad campaigns on a weekly basis to promote Facebook competitions

- each channel posted 3 times a day, resulting in more than 200 posts daily that needed monitoring and approving

- keeping the content calendar up to date including 12 main promotions a year and ensuring assets including images and videos for all channels were created well in advance by the agency

Other marketing duties included website updates, press releases, overseeing creation of promotional videos for new stores, ordering shows for in store radio and ordering content for the in store TV.

Global Social Media Manager

Shakeaway Hastings

Owner and manager of the Hastings branch of the Shakeaway cafe franchise. This role has given me lots of experience in running an SMB and I saw first hand the power of social media marketing to drive customer visits into the store. I've used social media for business since 2010 when Facebook business pages were new and started running Facebook advertising as soon as they launched newsfeed ads.

Facebook, Instagram & LinkedIn Ads Specialist

Welcome! 👋 My aim is to help companies rapidly scale by getting them more leads, sales, revenue and brand awareness using Facebook, Instagram and LinkedIn social media advertising 🚀🚀🚀 Here's a few key facts about what I do. 

1) Every year I personally manage close to $2 million of ad spend for clients and have booked well over $10 million of ads in total. 

2) My previous role was at Hootsuite, the world's most used social media monitoring tool. I'm now running ads for clients on a freelance basis through my own agency, allowing me freedom to use a wider set of tools to help clients succeed. 

3) At Hootsuite I mainly worked on the AdEspresso ads platform. AdEspresso were Facebook's largest Marketing Partner and a Google Premier Partner due to the large volume of ad spend we processed. 

4) I’ve audited campaigns from over 1,000 ad accounts, allowing me to see what works and what doesn’t across a range of industries in dozens of countries. 

5) My coaching clients range from solopreneurs spending $20/day on ads up to corporations with $10+ billion yearly revenue, I can adapt my coaching strategy for all levels of ad spend and sizes of teams. 

6) Every month I used to run AdEspresso’s $1,000 experiments where we discovered what’s actually working now by putting $1,000 of ad spend behind an experiment. 

7) I presented the AdEspresso webinars and Office Hours calls, previous guests include the official Google team, Mari Smith, Dennis Yu, Molly Pittman, Larry Kim and Andrea Vahl.

8) To help as many people as possible succeed with their digital advertising I have written dozens of blog posts as well as given talks, appeared on podcasts and run both free and paid for training courses. 

9) I’m Meta Blueprint certified which is the only official Meta Ads certification, and hold all 11 Digital Marketer certifications along with several Hootsuite Academy and Google Ads certs. 

10) Before specialising on the paid side of social media, my previous role was as a social media manager for a global café chain, which involved coordinating the marketing for over 70 social media channels. 

11) I'm based in the beautiful seaside town of Hastings (yes, the one famous for the Battle of Hastings in 1066) on the south coast of England. I mainly work from my home office with the kitty gang of Jeremy, Kevin and Colin, the chances are at least one will appear if you’re on a call with me! 😸😸😸

If you have any questions about your ad strategy or if you work in digital marketing and want to geek out about what's working now with paid social please drop me a message.

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The Battle

Nick Telson-Sillett

Paul Fairbrother

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