Are you stuck? Are you frustrated that things aren’t moving faster? Are there too many decisions to make? Are there too many ideas to consider?
Do you feel alone? Do you make plans and not stick to them? Do you miss someone asking you the hard questions? Is there no one to bounce ideas off?
Do you know what you don’t know? Do you know what you need to panic about not doing? Do you know what you can safely put off till later?
That’s a lot of questions. If you are like many of my mentees you’ll be nodding as you run through them.
Typically you are super smart, hard-working and with a lot of experience in business. If you have a co-founder they are likely to be good at tech, but not a great foil for the business decisions you have to make.
The important thing is you want your startup to work. You don’t want to put years of effort, and your savings in, and not get anywhere. Even worse you don’t want to give up. It’s even harder when a spouse is putting a brave face on as they support you; harder still when they aren’t.
Every single point above I’ve faced, failed, survived and solved.

What does a startup mentor do?
Startup mentoring does a bunch of things.
- support
- knowledge
- contacts
Being an entrepreneur, running a startup is insanely tough. There’s always more that you can do. There is always a reason to work harder longer hours. Part of my role as a mentor is to help you judge when to suck it up and push harder, and when you really need to take a break and recover.
In most businesses, it’s clear what you need to do to succeed. Increasing sales and margins have many clear well-documented paths in most industries. As a startup for a long while, you may not know who your customers are, what they want or what you are going to sell them. There are lots of tools that help you do this faster
Finally, a startup mentor typically knows a lot of people. Potential customers, suppliers, employees, investors and more. These contacts and relationships are often the difference between banging your head against a brick wall, and smoothly closing your first deal.

How does startup mentoring work?
Startup mentoring is normally weekly or fortnightly. It’s a regular face to face meeting or zoom call. At the start of each session, you talk through what’s been happening, report any metrics and talk about how things that were covered in the last mentoring session are progressing.
Sessions work best when you bring a set of questions or challenges. Sometimes they can be solved in a few minutes. other times we come back to them month after month. In either case, you describe what the problem is. The mentor then asks probing questions to try and understand the problem and perhaps the underlying challenge that the mentee isn’t aware of.
Most problems aren’t easily solvable. The startup mentor will often introduce new ways of thinking, different models, and examples from their experience. Where appropriate he/she will then give specific advice on what to do next.
The real skill of a startup mentor is quickly understanding the information you provide and then seeing the core of the problem; then forcing you, in the nicest possible way, to take action to solve the key problem not the fluff around the edge.

How do you choose a startup mentor?
Here are a few points to consider when choosing a startup mentor
- experience
- expertise
- trust
- challenge
- domain expertise
- language
- stage
A startup mentor needs to have run startups. If they haven’t been the CEO or Founder then they haven’t been through what you are going through. That empathy based on experience is important. having done the job they will have also faced many of the same problems, and know what the solutions are and where to find them.
There is a reasonably well-established set of startup tools around what we call Lean Startup. If the mentor doesn’t know these, hasn’t taught them, and can’t guide you in their use then they will underdeliver. The ideal startup mentor will mentor and deliver accelerators for one of big VCs – Y-Combinator, Techstars and 500 is good experience to look for.
Trust is critical. You and the mentor are going to be working on everything that is going to be at the core of your billion-dollar company. Sometimes you are going to cry on their shoulder. She needs to know a lot to help you, and if you don’t trust her, then you can’t give her enough info to do her job.
Challenge is important. Your mentor is there to challenge you. The harder you work to justify what you want to do in mentoring sessions the better the quality of everything that you do. If a mentor isn’t asking you hard questions they aren’t giving you enough value.
Domain expertise. Your startup mentor doesn’t need to know much about your industry. You may have a business mentor to give you industry-specific knowledge. Your startup mentor provides knowledge and advice on how to start and grow a technology business. These kinds of businesses have similar problems across industries. The possible exceptions are medical devices due to the market and regulatory structure. Most startup mentors will have worked with dozens of startups in your industry
Language. Working with someone in your native language is best. If you aren’t fluent in your mentor’s language then you need 30-50% more mentoring sessions to get the same results.
Stage – startup mentors tend to specialise at different stages based on their experience. There is a huge difference between the problems faced pre-seed and Series B, between pre-product market fit and ate stage growth
Humility – There is always more that startup mentors don’t know
What does successful startup mentoring give you?
I wondered about this for years. As an engineer, I like numbers and metrics, as you’ll discover. Mentoring sometimes seemed like a nice chat with no measurable outcomes.
What I see in my mentees is this
They move faster. Even when we don’t solve problems together, we do exclude bad solutions quickly. That increases the speed at which you do everything.
They are more confident. Because decisions have been made thoughtfully and risks have been managed they don’t worry or try and second guess.
They execute better. With less anxiety and stress performance improves. There are fewer unforced errors, and far more is right first time.
They make better decisions. Talking them through, cutting to the core and identifying the best approach pays dividends
They know more. They have more tools, insights and methods to use. This makes almost every challenge easier to overcome
Every single one of these points improves the metrics that matter to the business. So I don’t worry any longer if I can point to the change I’ve created. My mentees do.
One final point – there is an insane correlation between the number of sessions and the impact. Mentees who skip sessions frequently fail at 3-4 times the rate of those who turn up to every session.

Mentoring with Denis
I’ve had over 1,000 hours of mentoring rated by entrepreneurs, intrapreneurs and client managers. Every single one has given me a perfect score so far. I don’t expect that to last. Someday someone won’t like me.
Why do my entrepreneurs score me so highly?
I don’t come into sessions knowing the right answers. I let you take the lead with what concerns you, and then we work together to find solutions to work for you and your startup.
A lot of entrepreneurs say that they like the way I make them connect the dots in different ways, my energy and enthusiasm.
Others talk about how I motivate and inspire them.
You may feel like this, or I may leave you cold.
The only way to know though is to have an introductory call to see whether there is a fit

Pricing
Which plan should you choose?
If you do a lot of delivery choose the cheapest. Meeting more than twice a month will give you too much to do and think about on top of everything else.
If this is your first startup/business go for 4/month for 1-2 months and then drop back down to 2/month once you get momentum.
If there is a lot going on, and you need feedback and advice quickly choose the premium package. The support calls are only 15 minutes, but I will normally be on the phone to you within a few hours (scheduled calls permitting)
If you aren’t sure which is right for you, don’t choose until you’ve had a chat with me.
I do discount these rates for some entrepreneurs – typically in developing countries or where you are running a B-corp/ Non-Profit / Impact / Charity. It’s a gift from me.



