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Practically every startup founder has or is on the hunt for investors to seed their vision. While the wrong ones won’t necessarily ruin a company’s chances, the right ones can make your life as a founder infinitely easier through those all-too-critical initial sales. Below we look at five areas of alignment between a founder and investors and then explore five common returns entrepreneurs want from their investors.

A lot has been written about what to look for in an investment, a founder and a company, but a major part stays in the relative shadows; what founders should look for in their investors.

As an entrepreneur, I’ve found that while they are scrutinizing you, you need to be equally as diligent in learning about them. One of the magic beans to growth is having a group of seasoned, understanding, early-stage investors on your side who can turbo charge your company’s growth. Startup business is all about people in the early stages, expertly building the correct mix of development talent and product management and sales and executive strategy. Topping this team off are investors who believe in the vision, the founder and the opportunity. When all the pieces fall into place the chances of success skyrocket.

On the inverse side, if the investor is not right for you – maybe they see a quick exit but don’t believe in the vision – then the results can be disastrous.

Before signing with an individual, an angel group or larger investment organization, consider what you want to ensure your investors are aligned with you and your company.



1. Vision & Values

Many investors take an aggressively active role in startups. There’s a fine line between offering wisdom, insight, and productive thoughts and flat out taking over the direction of the company. Taking the wheel and driving the vision isn’t what you’re looking for. You need investors who understand that you’re going to make mistakes. The goal is to avoid as many as possible, but they are guaranteed to happen.


Sharing common values not only affords quick bonds of professional friendship but can help cement the right type of corporate culture early on. Having strong alignment on values will radiate from the top giving your employees a clear understanding of what the company stands for while providing the leadership to follow through on them.


2. Trust

Startups are an emotional and financial roller coaster. You’re up, you’re down, you’re upside down, wait, how did we stop sideways? Through it all, you need to remain positive, optimistic and focused Easier said than done. You’re a founder, but you’re still a person who experiences negativity, pessimism, and depression, which the startup ecosystem is finally starting to address.


Many entrepreneurs keep these feelings suppressed (I know I did, a lot). A great investor is someone you can confide in during these tough times of the journey. Trust, transparency, and understanding are some of the most powerful qualities an investor can bring to your company.


Do you trust your investors with your rawest emotions? Will they trust you to be honest about everything happening in your startup? The sooner trust, true trust, and transparency can be established, the sooner your investors can jump in to help when problems arise. 


3. Goals

Not everyone company is looking to become the next unicorn with a flashy exit and their face on the cover of Fast Company. In fact, most entrepreneurs start their businesses because they want to change the world, and they have a unique product/solution that they believe can do just that. Entrepreneurs have a burning fire inside that drives them to take smart (and sometimes foolish) risks, but those risks are all in service of the common goal of success. The right investor will be aligned with your goals and plan.


They will not act as a force to push you in another direction, or question your ultimate goals – they will challenge your assumptions and question milestone goals, which is their job as a proverbial ’third eye’ on the company – but will help you establish attainable goals that service the ultimate vision.


4. Their Desired Role

While you might have already formed a complete picture of who your investors are, and what role they will play in your startup, it’s important to understand where they are coming from. They will undoubtedly have their own concept of what role they are to play and sometimes those visions are not in alignment. Ask yourself, does your investor need to be:


Active: Someone who is intimately involved in the business, on a near day-to-day basis. Someone who has the company’s best interests at heart and believes in it so much they’re essentially a co-founder?


Passive: Someone who can help finance the business, but has no desire to be involved in the operations and would prefer to receive quarterly (or monthly) reporting on the health and growth of the business?


Advisor: Someone who can be involved on a weekly basis? Someone who can work with the executive team to help guide them through the weeds?


CEO Mentor: This is someone who could actually encompass an active investor and an advisor. Someone who has an active interest in the operations of the business, but takes a specific interest in growing the CEO’s potential so they can slowly extract themselves from the operations as the CEO realizes their own skills to effectively lead the business to scale. 


This type of planning comes out through conversations and building the relationship while bringing the prospective investor into the fold. Just remember to go into these conversations with an open mind and flexibility so you can both aim to meet in the middle, or better yet, on the founder’s side.



5. Positivity

Everyone is happy at the start, but how we act under pressure reveals our true selves. This could not be truer when dealing with someone who has put their own, hard-earned money into your venture and trusted you to produce results. Aligning yourself with someone who has a positive outlook, and knows that there will be ups and downs can help be a steady hand when things get rocky, but also a much-needed boost of enthusiasm for beleaguered founders in times of need.


Now you have an idea of how you should be aligned, it is time to ask, what do you want from them?


1. Strategic Expertise

Strategic expertise is real-world experience. An amazing MBA GPA doesn’t count – theory and case studies are great, but clean hands don’t build buildings. You want someone that has gotten their hands dirty. They’ve lived on instant ramen and spent years of their life building something great. They know what it means to be an entrepreneur in practice, not just in theory. 


The best investors leave decisions in your hands and respect your authority as CEO, but they’re also not afraid to speak their minds and voice thoughts and concerns that they’ve amassed through experience. If they’ve invested in a company like yours before – or even run one – then they’ll have first-hand knowledge of the various pitfalls and opportunities that lie ahead of you.


To become an entrepreneur is to embrace failure every day. An experienced investor has made errors of their own and typically, they’ll be able to tell you how to avoid them. If you’re going to make mistakes, they might as well be new ones! An investor who has ‘been there, done that’, is the one you want behind you, championing your company.


2. Contacts

The importance of this one is self-explanatory. A robust network of connections within your company’s industry can help quickly forge important early partnerships and customers to help make your first sales. As a founder, you should reach out to investors who have specific industry connections in your specific industry segment.


An investor who has 10 years of experience in your industry is far more valuable than an investor who has 30 years of experience in a completely unrelated industry. Do your due diligence on any investor you’re speaking with and figure out who they know and how long they’ve known them – these could be your key connections moving forward. Platforms like LinkedIn, AngelList, and good old-fashioned telephone calls are your best bet here. Don’t be afraid to ask about the connections you consider valuable. While LinkedIn might say they’re connected, they might have met once at a conference but cannot offer any more of an open door than a direct message via Twitter could offer.


3. Successful Track Record/Serial Entrepreneur

Ideally, you will find an investor who has either been an entrepreneur themselves or has invested in early-stage companies that have gone on to be successful. If they’ve built a company that has successfully exited, or if they’ve invested in a company that has, they will know what it takes to punch above their weight and scale a company to success.


Having an individual with a reputable name as an investor or serial entrepreneur can afford your company a sense of competence and prominence in the marketplace that could have taken years to build up if you follow the bootstrapping path to growth.


If your investor can point to past successes in your industry or other relevant industries, that should give you confidence that they’re good to work with. Even better if they can point to specific examples of how their influence helped businesses like yours grow and achieve their potential.


4. Mentorship

Particularly in the early stages of your relationship with your investors, you will need to be comfortable working with them on a fairly regular basis, taking the opportunity to become a sponge for knowledge and knowing how to manage their expectations and their opinions about how things should be done. While the ultimate decisions fall to you as the founder, there will be certain situations where your investor’s experience will be far greater than your own and you’ll need to let them call the shots (behind the scenes). Taking this opportunity to learn and be mentored by someone who has been there and done that can tremendously aid your development as an entrepreneur – after all, you don’t know what you don’t know.


However, giving up the reigns can sometimes be difficult for founders, particularly first time entrepreneurs who are used to making all decisions. The test for this is to ask yourself when speaking to potential investors if you would be happy working for them if they were the ones running the business. If you wouldn’t be comfortable with that, then they may not be the investor for you.


5. Straight Talk

Entrepreneurs are emotionality invested in their business, how could you not be! This is your baby, you conceived the idea, poured many sleepless nights into forming it, took the risk to strike out on your own and have grown it to today. 


For many founders, their company becomes a part of their personal identity. This makes it very difficult for entrepreneurs to step outside of themselves and think about things from an objective perspective. Great investors help the entrepreneur see situations from a different point of view. They’re able to present the third eye approach to problems and give you the straight goods on where the pratfalls may lay, and more importantly, advise on the best course of action to find the right solution. 


They know you’re personally invested, but they’re financially invested so it is in their best interests to give it to you straight and quickly so that solutions, pivots or dodges can occur and you can get on with building the next unicorn. 


While these are some of the areas of alignment and wishes to have in an investor, by no means is this a complete list. Each company has its own unique needs and requirements. Each investor has their own checklist for due diligence on a founder. It is where they meet in the middle that the great partnerships are formed and the founder and investor work together to build to scale. 

Want to learn more about how your company can benefit from an experienced creative professional? Click below to set up your 30-minute consultation. We’ll sit down and work through your branding, marketing, or creative materials to find where you need some work, and offer our suggestions.


“That seems like a lot for a freelancer, why don’t we find a cheaper junior option?” And with those words, the start of the project from hell came to be. Not because the project had crazy requirements, but because in the quest to save some cash, a founder hired a lower cost freelancer only to get stuck in revision purgatory and with it, a vicious final bill that was over triple the intended project cost. 
Lots of entrepreneurs face the dilemma – hiring in-house or freelancer? Junior or senior? Think about it in this frame:
• You can hire a full-time senior creative (designer, writer, etc…) for $120,000 per year,
• You can hire a freelance senior creative for $120 per hour.
What is right for your business, of course, depends on where your business is. Some examples of when it’s time to hire a freelancer, and if spending less is a good idea are:
• Have you started marketing?
• Have you raised a Series A?
• Is your internal marketing team stretched beyond their skill sets?
• Do you need a part-time Chief Creative Officer?
• Is your brand strong, or is it time to build a professional, robust brand?
• Is advertising part of the plan?
Saving money is great, but there are discernible downsides when it comes to low-cost freelancers, such as:
• Saving money, but quality could be questionable,
• Saving money, but revision costs could eat up any savings,
• Saving money, but projects could take longer due to misunderstandings (and not knowing when to ask for help),
• Saving money, but no oversight that your freelancer is billing accurately,
• Saving money, but dealing with a junior that doesn’t know what they don’t know, and you end up paying for their education.
Most creative freelancers on the market are senior talent, individuals who have honed their skills over the decades working in agencies, production houses or studios. These creatives have seen it all, and have a wealth of experience and knowledge to draw upon. Most importantly, they know what they don’t know and are not afraid to ask questions. 
The disturbing trend recently, with the advent of Fiver, Upwork or 99Designs (to name a few), is that juniors are joining the ranks of freelance creatives. While they have great ideas and undoubtedly skilled portfolios, they lack experience in dealing with clients. Worryingly enough, their confidence masks that they truly don’t know what they don’t know, so they don’t know what questions to ask. This is where revision purgatory starts.
Consider this low cost scenario: The project starts off well, the work produced looks great on screen but then all of a sudden when part of the project needs to live in the real world – away from screens and on printed pieces – the colours look dull, the front and back don’t align and the fonts didn’t work. Everything now needs to be reformatted and reprinted. Costing you not only double in print costs, but also in revision costs, not to mention your marketing team’s time in dealing with everything. It turns out your junior freelancer only has experience in digital design and has never produced for print before. 
While a company might see savings through junior talent, those savings can be eaten up through miscommunications, excessive rounds of revisions and overall poor client/project management. All of a sudden the senior creative seems very reasonable and might be the best solution to troubleshoot the project to completion. 
To help pick the best solution for your company, start by doing a thorough portfolio review. Quantity does not always equal quality, and most top creatives will only present a handful or projects; the ones they are the proudest of. When interviewing a junior, their portfolio might look great, but how do you know it is their work? Always ask specific questions about their creative rationale. If it’s shaky or doesn’t add up, they might have plagiarized it. Ask to see a copy of their creative brief. This is the window into their thinking by learning what type of questions they ask of you, and how deep are they willing to dive to learn about your needs? You can also ask to read testimonials or references from their past (or current) clients to understand what it is like working with them. As seasoned marketers, you know what flags to look for in this process.
At the end of the day, there is no one-size-fits-all solution for producing creative marketing for any company, however, there are steps you can take to decide which freelancer is right for your business – junior or senior – and what the ramifications could ultimately be when discovering that you truly get what you pay for. 
Do you have a creative project that needs troubleshooting? Or are debating what freelance option you should look for? Click below to set up your 30-minute consultation. We’ll sit down and review your needs, find the holes and propose solutions to get your brand on track.

“We really need some design help on this! Should we get an agency, or does anyone know a good freelancer?”
This phrase has been uttered one way or another in practically every startup’s office within their first year of business, and it leads to the common dilemma, agency vs. freelancer?
In my career – which spans running an agency, working as a freelancer, and helping startups as an advisor and consultant – I’ve heard this question countless times. Unfortunately, there is no one-size-fits-all answer. However, there is a framework that I use to help startups decide what kind of design help is right for them.
All too often, companies start by evaluating different freelancer and agency options without really understanding their needs. Just like starting a marketing plan, you need to know where you want to go and have defined goals before you can know which content outsourcing option is right for you.
The first thing you need to do is understand the difference between the two:
A freelancer is an individual who is self-employed. They are selling a specific service to you and are usually the only person working on your project.
An agency is a full-service team. They will provide you with an account manager to manage your business. They then have a team of designers, art directors, copywriters, media buyers and strategic planners at their disposal.
What Does Your Business Need?
The next step is to ask yourself (or your team) some questions about the project and consider the following:
  1. What kind of work do you need executed?
  2. What is the size of the project?
  3. What is the complexity of the job? Does it need an efficient team or can it be achieved by a skilled individual?
  4. What is the budget?
  5. What is the timeline? 
From these 10,000 foot questions, you can dive into the deeper questions that are applicable to your specific situation. These don’t necessarily cover all the questions but are a good start for branding, marketing and product development.
  1. Do you need a logo? Are you looking to establish your brand? Do you need a complete visual identity to reinforce what the brand means?
  2. Do you expect an informal deliverable (e.g. a logo with rough brand guidelines) or a comprehensive package including brand vision, voice, and use guidelines?
  3. Do you need help with the content, messaging, and structure of your marketing website?
  4. Do you need help with your social media strategy? Do you need support over time to execute that strategy?
  5. What about advertising, email campaigns, product videos, analytics, or marketing insights?
  6. Do you plan to build a marketing department internally, or are you focused on product design and engineering?
  7. Do you know what problem your product is solving, and for whom?
  8. Do you need help designing and testing your product?
  9. Have you figured out how all the pieces are going to fit together — stories, content, screens, UI/UX,  video, animation?
  10. Do you need a polished, sophisticated product at this stage? Or just a basic functional interface that will capture the attention of users and the imagination of investors?
With answers to these questions, you can limit your search to the agencies and freelancers who specialize in the kind of work you need. Listen to what kind of work they say they do, but don’t forget to look at their portfolio for concrete examples of the kind of deliverables you expect.
Where Are You As A Business?
Once you’ve figured out what you need, you’ll want to consider the state of your business — size, stage, culture, etc — so you can look for help that will be a great fit.
Traditionally, creative teams evaluate potential clients along three main verticals, which you can also use to evaluate your business as well:
How fast is your business growing? Is your primary focus to continue feeding and accelerating growth? Or do you plan to evolve more slowly, refining the technology and product while looking for the right application along the way?
Where is your company headed? Are you offering a specialized product that’s aiming for a specific result? Or are you defining a new business, paving the way as you go? Or maybe your business is so disruptive that it will affect an entire culture.
How easy would it be to shift your focus if you identified a more attractive business goal? Would you be slowed by infrastructure, investors, team, or culture? Or would you be able to react nimbly to the new opportunity you identified?
Finding Your Solution
Let’s use your answers to find a good starting point for your search. Here are a few examples that should help you decide where to look for your company’s design needs.
Big Agency
Our company is focused on a clear target market (direction) and we need to move quickly (agility). We can’t afford to make mistakes. We’ve passed our Series A and are well funded. We need an experienced team that offers a range of top-level services. 
In this example, your team probably needs a big agency.
Small Agency 
Our company is growing rapidly due to unexpected demand, but we’re not quite sure where we’ll level out, or how our focus may change along the way (pivot anyone?). We’ve received our seed financing, and have had a couple of bridge loans to help us along to our Series A. We need a team that can run with us, adapting as needed and growing with us. 
In this example, your team probably needs a small agency.
Our company is just got our seed funding. We have a really great idea, but the target market isn’t entirely clear. There’s not a major sense of urgency or competitive pressure to go-to-market, we need to make sure our product-market fit is right first. We need a partner who can help us explore and experiment with limited cost and uncertain expectations.
In this example, your company probably needs a freelancer. 
Big Agency
A big agency has over 100 staff, usually around 250 – 500 in each office and are frequently (but not always) multi-national corporations with offices around the world that can pull from a massive network of talent and media connections. They tend to service Fortune 500 type brands and mostly produce consumer-facing traditional advertising and branding solutions.
Small Agency
A small agency is usually fewer than 50 people – lead by a team of experienced senior specialists who in turn lead smaller teams of junior and intermediate account managers, art directors, copywriters and media planners. They frequently call in support for photography, animation, video production, audio production and other specialist skills from trusted freelancers with whom they have long established relationships.
A freelancer is usually a highly skilled senior specialist (design, copywriting, front-end development, photography, video production, animation, etc) who has established their career in big and small agencies over a 15-20 year period. They know their craft and can help guide you along acting not only as a hired gun, but as a mentor to educate you and your team on their specific discipline. 

However, not all freelancers are senior specialists. More and more frequently freelancers are bidding on jobs with only a couple of years experience in the industry. These are the ones to watch out for, their lower cost might fit your budget now, but the long-term cost in foresight planning, revisions and mistakes can end up costing your company multiples of the initial project fee. This is a much larger topic, which I’ll be discussing in a couple of weeks in a blog focusing on the tradeoffs of spending less on writing/creative (and is it worth it).

Want to learn more about how your company can benefit from an experienced creative professional? Click below to set up your 30-minute consultation. We’ll sit down and work through your branding, marketing, or creative materials to find where you need some work, and offer our suggestions.


We’ve all had that client. The one with a huge, last minute, complicated project and then try to play the role of ‘worst client ever’. They do things like neglecting to answer their phone or email, love to change their minds about details in the brief, all the while demanding that you do the impossible in a matter of minutes. Of course, they forgot to mention they expect you to do these things free of charge.
Clients like these are ubiquitous in the world of freelancing. Most freelancers will work with at least one crazy client at some point in their career. They’re the fun vampires, sucking the joy and creativity out of a job that can leave you wondering why you didn’t go to law school or go work in a bank.
However, to keep the lights on, you need to listen and work with your clients. Here are some tips to keep projects on track, and some sanity in your mind.
1. You Are Clear About Out-of-Scope Work
There’s an easy way you can mitigate the problems caused by bad communication in a project. One of the most frequent complaints have to do with time. Designers rightfully take issue with their clients expecting them to be time wizards, completing an impossible amount of work in the space of a day, or hours that they don’t want to pay for the extra time.
So, what do you do? In your project contract (there should always be a contract between you and the client), include a clause which breaks down your expected compensation in the event of a rush job or any overtime work. Better yet, include a line on your rate card highlighting rush job pricing, this way there is no ambiguity on what the price is for rush jobs.
Make it very clear to them what they’re asking for and how difficult it is to accomplish, when they want you to redo the web page layout of the site to a two-column layout from a three-column layout, for example. If you’d rather not be stuck doing revision after revision, include a set number that you’ll allow each client to have.
Be specific about the project’s deliverables and outcomes, and protect yourself by having solid terms and conditions agreed to in the event of out-of-scope work arises. When the guidelines and parameters for what you will and won’t do are set in stone, it does wonders for your peace of mind.
2. Your Quote Contains A Contract
If your quotes don’t currently contain a contract, don’t take on another job without one. You can find free quote and contract templates all over the Web that cover a wide scope of freelancing needs. Here’s a good starting point from LawDepot that you can use for free.
The best solution, however, is to simply consult with a contract attorney and let them draft your company’s business contracts. If you’re intimidated at the thought of going to a lawyer, don’t be. I promise you, it’s not nearly as scary (or expensive) as being faced with a mountain of revisions from a client who isn’t legally obligated to pay you for your extra hard work. You can find great lawyers that know small business by searching Click Lawyer.
3. You Win The Presentation
Give the client what they’re asking for (for the most part). You’d be surprised by how much clients will allow you to get away with creatively, as long as you’re able to sell and rationalize it to them. The key is how you present your work and your ideas.
A mediocre idea that is presented well can outperform a great idea that’s presented poorly. So naturally, a great idea that’s presented well is the winning combination. Spend a few minutes to get inside your client’s head. Talk to them, listen carefully, figure out exactly how you need to package your ideas so that they will choose the option that’s best for their needs.
Do your research and present your case clearly. Support your design decisions with data. You could, for example, use usability research results to back up your choices. Yes, this takes a bit of extra effort, but it’s almost always worth it.
4. Your Portfolio Represents Your Business
You want to make sure that every single piece of work in your portfolio is tailored to the needs of your ideal client. This helps to make sure that you work with client’s who best match your work, acting as a sort of filter against clients that you might not be the best idea.
If you’re trying to attract small businesses or startup companies as opposed to Fortune 500 companies, build a portfolio that is attractive and focused on the needs and wants of these businesses. If you work well with a high-end client, you’ll need to adjust your portfolio so caters to this market. If you don’t have any work that represents the market you’re looking to attract, then take the time to create some fun spec work that showcases your ability to work within that market.
5. You are an Educator
Another important hat for designers to wear is that of the educator. We’ve all heard of the clueless design client who has no idea how to download an email attachment, much less understand the ins and outs of what’s required to complete their project.
I’ve found that having patience with people and taking care to explain in detail what is expected from them has helped me avoid quite a few catastrophes in the past.
If you struggle with being able to communicate difficult concepts to your clients, consider making overview presentations and inviting your client to join you for a lunch and learn. This not only helps build trust between the two of you, but it allows the client to have a no-pressure atmosphere to ask questions without distractions to learn about the creative process, your role as a designer and their role as the client. This is also a great opportunity to teach them about the importance of the brief and how the two of you can work together to define the scope before jumping into a new project.
Being able to communicate clearly can help defuse a situation that might otherwise get out of hand and end in frustration for both you and the client.
6. You are the Underdog
Here’s a personal antidote from my days as an in-house designer. I’m one of those people who can produce a large amount of quality work in a relatively short amount of time. Because of this tendency, I’ve found that freelancing suits me far better than in-house work.
Firstly, it allows me to have near complete control of my own time. I’m no longer chained to a desk, droning away with lame busy work that has nothing to do with anything creative – or more accurately, looking busy to burn the hours when there’s nothing to do.
Secondly, and more importantly, it allows me to keep my speed and creative process a carefully-guarded secret.
When you produce a lot of work in a short amount of time, you tend to assume you’ll be rewarded handsomely for it. Unfortunately, most people figure out pretty quickly that that’s almost never what actually happens. Most likely, you’ll just be loaded down with more work. Once people find out how fast you are, they’ll get spoiled and will start expecting the same level of output from you in the future.
As many designers can confirm, it’s almost never the actual work that takes the most time. You’re a designer – you know what you’re doing and how to use your tools. The biggest time drain is usually getting the client to be on the same page as you are in terms of the idea.
As a Creative Director friend likes to say, “When a client asks how long it took to come up with the idea I like to say ten years and five minutes. Ten years to gain the experience to learn how to create quickly”. 
If you’re a freelancer, my crazy suggestion to you would be to slow down. Not “slacker” slow, but try not to let your clients in on your amazing superpowers. Impress your clients by under-promising and over-delivering.

Want to learn more about how your company can benefit from an experienced creative professional? Click below to set up your 30-minute consultation. We’ll sit down and work through your branding, marketing, or creative materials to find where you need some work, and offer our suggestions.