Stephanie Hayes Startup and Small Business Mentor, Entrepreneur

Awesome question.

I'm going to avoid the "cell phone, laptop, internet connection" and assume they are givens so I can focus on the meaty stuff.

I'm in my second startup right now and using what I learned to do this right this time.

1. Good partner(s). Going it alone, or with someone that does not have your interests in mind, is hard and harder, respectively. Partners give you a sense of shared ambition and they are the only others who have the same level of motivation and dedication as you do. I started my first business with a less-than-ideal partner and it dragged me down the whole way, cost me a tonne of money, and prevented us from making the company as successful as it could be.

2. Experienced mentors or advisors. I triangulate when I need advice or have to make a big decision. I speak to at least three people that I trust who have done what I need to do, and pick out the commonalities in each response. This works especially well if they all have diverse experiences and personalities and you recognize their angle.

3. Financial awareness. Wow, this is a big one. While you don't need to be an expert in tax accounting, you sure as heck should know about what is going on in your business. What are your obligations and what do you need to plan for? What does it mean when you receive payment, or sign a contract? When you look at your books, can you explain where all your money is going and why? Can you speak to your accountant and understand why he/she is structuring your books in a certain way? NOTHING will make you fail faster than having your head in the sand when it comes to projections and budgeting, and cash flow management for that matter. Hire good people to manage the details but make sure you can understand them.

4. Sales partners. By this I mean relationships with other organisations in your industry who can help you sell your offering. I structured more than 70% of my sales through partners, who would benefit from any sales they drove, and who were much, much bigger than myself with broader reach. It's like having a mature sales organisation that you don't need to pay for, and they will introduce you to clients that you couldn't otherwise meet.

6. A proven business model. Don't skimp on relentlessly proving that someone will buy what you want to sell, and will feel relief and delight that you've solved a problem or filled a gap. If you can't say you have done this with confidence, stop immediately and invest in this activity.

Selling your services will also take a while to get paid. If you are a consultant, unless you can establish a retainer agreement, you will still be 60 days before you get paid.

Honestly, you need to sell "stuff" if you need immediate income. What can you make or craft? What kind of information products can you develop quickly that people will buy online?

You need a strategy like this while developing a possible services offering/clients. You may need to even just get a job that will pay you every two weeks and develop a new venture on the side.

Unfortunately, nothing comes free, quick or easy. Develop a plan to get back on your feet, but in the mean time find something that you can make that you can sell in a cash exchange transaction quickly.

Most of the startups that I have mentored have gotten to their customer discovery/value proposition phase where they are required to prove or disprove their value proposition and they freak right out because they want a list of interview questions.

I always tell them to ditch the questions. Approaching customer discovery with a list of questions will completely limit your responses by setting their thinking around a specific solution and then you miss understanding if your solution is even an answer to the problems they *really* have.

Instead, go back to what is prescribed in the customer validation approach and do a "day in the life" analysis. Don't assume you know what the problems are. Start with a hypothesis and then go to your customers and ask them to describe their work processes, or their buying habits, or whatever it is in the context of your product, but let them drive. Most times, they will quickly get to describing what's challenging about this process and the first things they will describe are the biggest pain points. Of course you want to be armed with some questions you can ask to drill down further, as described in some of the responses above, but listen, listen, listen. Guide them and let them talk. People will complain more than they will rave and with a skilled facilitator or business analyst, you will be able to maneouver the conversation to discover whether they actually care about the problem you think you are solving or whether you need to pivot your offering/value proposition to address what they are *really* struggling with.

Bottom line - ask them to describe their life in the context of your offering. Don't lead them to focus specifically on your solution right off the bat.

Some great responses here that I won't try and reiterate, but the one model that hasn't yet been mentioned (at least from my reading) is a hybrid model built on the ages-old business advice around keeping your core capabilities internal and outsourcing the rest.

If I were in your shoes, I would be hiring or partnering with a technical architect who can craft the design of the technical solution with aligned interests in mind (being a member of your team). Then, you outsource the engineering work based on whatever model works for you (personally, I would have the technical architect hand-pick resources), and use them surgically to deliver parts. This way you have the best talent to deliver the work they are best at, and your distributed model reduces the risk of theft of IP (although IP ownership is usually covered in a good contract).

You also need to decide if what you are building is actually an MVP, or if you intend on the resulting solution to form the foundation of your eventual product. If it's disposable, you don't need to spend a lot of resources getting to something that can communicate a concept. In fact, what you probably need for that is just a good UI designer who can build wireframes. Don't get too hung up on a fully functioning MVP. My best and most useful conversations have come from customers who see nothing working yet but can visualise the concept enough for me to get information on whether to stay the course, or pivot.

I would suggest that you do not distract yourself with trying to become more technical. First of all, the value you bring to the company is representing customer needs and the strategic direction of the product. If you become too mired in the technical details, you start making decisions based on technical facility as opposed to what you can offer the market. If you do not produce something that the market demands, you might as well shut down the company. Your technical leads will advise you on what is possible and reasonable, and you will always have that healthy push and pull between "desired" and "practical" and those two forces should work together to help you build a roadmap that serves both your customers and your business.

Secondly, your technical knowledge will grow organically as you gain experience building a product. I consider myself very technically well-versed but I am not a technical resource. I don't have any formal technical education but I can speak knowledgeably about architecture, platforms, design and implementation to a certain point at which I will actually be detrimental to my team if I try to venture into any further detail. I hired them and chose to work with them because I can throw problems and issues at them and they will design the best solution. I don't want to debate their technical challenges. All of my technical knowledge has come from years of working with technical teams and designing products. I have it, I like having it, but I never let it govern decisions I make as a product owner and manager.

My advice to you is to stay out of the weeds and do what your team needs you to do - advocate for the vision and the market potential of your product and let a strong technical lead drive the architecture and technical roadmap. You will be in constant healthy negotiation around prioritisation and a good technical lead will "get" the business demand and value and work to find the best plan for implementation.

Oh this is a long question to answer, but let me start with my experience. I'm the "outsourced COO" for a number of small businesses who have grown through their bootstrapping phase, proven they have a market and all of sudden start feeling the pressure of the business expanding. 9 times out of 10 what they need is someone to wrap their arms around all of the operational stuff, mature their processes, put systems in place, connect their data, introduce greater discipline in the production of their core offering, make sure they have the right service providers in place (lawyers, accountants, bookkeepers, etc.) and they can easily and quickly get access to the right metrics to understand how the moves they make affect their desired outcomes. This is an important and often ignored role and is the key to relieving a hard-working CEO of the things they likely don't do "well", and allow them to focus on building their business, usually on business development and strategy. I think it is smart for you to consider adding this to your roster, particularly if your time is better spent on more strategic work.

More and more I would say that sourcing this kind of talent from recruiters and executive head hunters is becoming ineffective. You are best to scour LinkedIn and use your personal network for recommendations. You are far more likely to find good people this route than relying on the "you get three options" approach that many agencies will offer. You know your business best and who is going to fit.

It sounds like you are still relatively early stages. Don't worry about titles. The right person will be someone who has been there before, in a growth phase of a company, and knows that titles mean nothing, other than to better define their scope of work and help the employees understand their role. If you find the right person, they will be able to tell you exactly what you need from an operational perspective. I fear if you try to turn this into a CEO role, you will find someone who doesn't want to get mired in the details and focuses on the strategic work (appropriately), so you will end up with the same problem. Go find someone who focuses on, and is excited by building the operational foundation for your company. Someone who is going to say "OK, go build your business. I will make sure everything works to support that." They should also know how to scale operations to meet projected demand so you can work as a well-oiled machine.

Additionally, look for someone who has run a company before. I certainly earned my stripes when I went through this myself. Your candidate should understand business process engineering, change management, resource management, service design, financial and data management, systems and technology, etc,

Don't skimp on compensation. Pay them what they are worth and make the offer attractive. You will lose senior resources in a heartbeat if they don't believe you value their skills and are ready to make them an integrated part of the team, and to trust in their experience. Senior resources are not motivated by money but by the challenge, the team, the knowledge that they can be successful.

I hope this helps. Happy to chat further if you have some more specific questions.

It's a well-discussed and accepted principle of entrepreneurship that founders benefit from being surrounded by people who can support them on multiple different levels. I recently read an article which outlines the five mentors a founder needs in her arsenal. I can't find the article specifically, but there are many out there that are similar (http://www.entrepreneur.com/article/225184). The gist of most of them is that you need to surround yourself with advisors that can cover you from all angles - business in general, your business specifically, you personally, your professionally, and from experience as a founder themselves.

This is a hard lesson for starting entrepreneurs because they tend to be either proud, intimidated, or not sure where to start. I only recently learned how powerful reaching out to others can be, and building my own advisory team. I did my first venture all on my own, and a big part of the reason I left was that I had no partners and had not brought anyone in to the fold. I was too proud. While I did relatively well for being on my own, I could have taken that company to a whole other level if I had sought the advice and experience of others who could guide me. To be honest, I think I was afraid to be successful because it meant opening my ideas and my business model to possible criticism when I had invested so much already. Big mistake.

Go and find VCs who are willing to have a chat and introduce you to the fundraising game. Go and find other entrepreneurs who have been there. Go and find other leaders in your industry who know it well and have battle scars from selling or building. Go and find professionals who are like you, and who are not like you. Besides the great experience and feedback they can give you, they all have networks and people love to help and be experts. Ask for as much help as you can get - if you need something, you will definitely not get it if no one knows you need it.

If you are offering advisory services only, you should propose a retainer structure, or a possible 50% retainer, 50% on milestones or completion. You could also do a monthly retainer based on the length of the project. If you are actually doing some type of implementation work, I would expect you could ask for a retainer/deposit and then bill the rest on time and materials.

How does your industry typically structure deals?
Will the customer focus on value-based billing or effort-based billing?
Are you managing a team of people?
What is your seniority and level of experience?

Without knowing more about the project, your experience, or the nature of the work, it's hard to answer this question but I would be happy to chat further, having many years of experience building and operating a professional services firm. There are many options around pricing models - the best fit depends on the project and the customer (and you!). Feel free to reach out to me directly if you would like to discuss further.

Well, Excel is still the world's number one ERP, but putting that aside for now, I would think that the biggest issue entrepreneurs face is finding IT tools that are relevant to the size of their business. They need to set themselves up to handle growth when it inevitably occurs, but many of the systems they would ultimately end up with when they are mature, are far too cumbersome and full featured to support a startup.

Therefore, they end up with tools that are really most suitable for freelancers or independents, and can only take them part of the way. Additionally, they often have trouble finding operational systems that are integrated (accounting/project management/time tracking/production management/resource management etc.) so they end up defaulting back to spreadsheets and Google docs to try and piece together a view into their organisation.

As an early stage startup, I would be expecting to track cash flow on a micro timescale, production/project management and cycles, profitability and customer acquisition metrics as these are the areas where there will be (should be) the most variability and evolution IF the data is available and the company can easily see where a pivot may be required.

I have helped a number of small businesses in growth phase, and startups, piece together integrated operations foundations that cost very little and provide a working foundation that will get them to the point where they start to see enough volume in their business that necessitates a transition to more robust systems. I've also worked with more mature organisations to take them through a software selection process once they are ready to mature.

It's natural for a startup to progress and mature its systems, but the trick is to set them up from the beginning such that the DATA is easily accessible and transferrable once growth happens.

Happy to chat further - feel free to reach out directly.

In addition to the response above, I would suggest that you may also want to look at whether the existing product lends itself to multiple forms of digital products. For example, could a published book in hard copy become an ebook, as well as a set of short videos, maybe an audio recording or podcast, or could subsets of the written piece become smaller, bite-sized information products in which the content is somewhat re-purposed for a specific niche or audience?

Digital products take many forms and each individual buyer prefers a different method for consuming your content. For example, I almost exclusively will listen to audiobooks vs. reading something because I have so many time constraints. If you can offer a suite of related products on platforms that are diverse, you have the best chance of reaching a much larger audience.