In Portland Ten, we have the opportunity to work hands on with founders for a period of three months, and with a cross-section of projects at the same time. It’s a really cool experience to have an in-depth view on several startups getting off the ground at the same time!

Overall, managing multiple startup projects at the same time makes it easy to spot common problems & patterns that high-energy, multi-talented, Type A, hardworking founders have– and to come up with ways to solve these in simple ways, to keep the founders & their projects on track.

Here are some common problems we see among early-stage tech founders– and some quick & simple ideas on how to solve them.

#1. No funds/money.

So, the most simple solution to this problem is to shift the way you think about starting or running a project, and remove "funds" or "money" from your perception as a barrier to the project’s progress. 

Start by itemizing the "things" you need in order to get and keep the business going– stuff, people, arrangements, momentum, a compelling value prop, customers, equipment, skillsets. Then generate alternate ways of acquiring/bartering/trading things you do currently have (assets) or can do (skills) in exchange.

In terms of assets, sell or rent things you currently own; in terms of skills, do consulting or part-time work to generate income, or barter your skills in exchange for someone else’s, that are needed for your project.

It’s less effort to think, "I need $X00,000 dollars to get this product off the ground, so meanwhile I can’t get much done, until I find an investor", but, it’s also much less likely to generate results and open up doors.

As literary character Violet Baudelaire says, "There’s always something." As an entrepreneur, it’s your job to find the "something" that will make things work. Always.

#2. No sales, or insufficient sales.

Some common reasons for no sales, or insufficient sales, include:

• No formal sales process in place
• Lack of consistent follow up sufficient to close the deal
• A product that doesn’t match user’s needs
• A product that’s not currently usable for customers
• The product doesn’t appeal to the customer
• Lack of sales skills or understanding of the sales process overall
• "Bootstrapper’s desperation" bleeding into the sales efforts & scaring off customers

Many founders are disinterested by the sales side of running the business. They feel like making money is not as noble as inventing or creating the product, or solving the problem users have, and so many highly talented people end up short-changing themselves through underemployment or running a "not-quite-for-profit" organization.

But the reality is that sales is an integral part of delivering a solution or product that users are willing to value and commit to. Sales is merely a process of demonstrating the value to the client and asking them for a commitment. It can actually be an exciting and interesting process to manage, and is critically necessary to the operations of a viable company. Tech founders in particular can shy away from sales because of the social/people component required, it sort of chafes against their natural skill set and preference for more technical, specifically intellectual activities like coding or product engineering.

One of the easiest ways to get a quick grasp on sales is to begin by analyzing a comparable "sales" process you’ve mastered in the past– finding a job, hiring someone, applying and being accepted to college, dating & marrying a spouse, or even just the way in which you make purchasing decisions as a consumer.

Then chart out a simple 4-5 step "sales process" through which you contact the client, download their needs & specific product feature requests, demonstrate the value of the product, and then ask for a commitment in the way of a business transaction, i.e. purchase, letter of intent, or contract. Commit to taking 20-30 users/clients through the process, and find out what they are or are not willing to purchase, and then revise your sales process from there.

#3. Frequent team conflicts.

This one comes down to two basic scenarios–

a. You have a high achieving A team, but you are managing them like a C manager

b. You are a high achiever playing an A game, matched with an underachieving C team

The stress level of a startup can be excruciating, and it brings out the best & worst in founders & early employees. If your team is underperforming, first check yourself and look at your management style– what can you do on your end to buffer the high stress scenarios, and get them to raise their game?

If you modify your management style to create an optimal work environment, but the team or specific members of the team continue to underperform, it’s time to address each situation individually to determine if the project or the role that employee is in, is the best fit for both parties.

#4. Not enough manpower or resources to get the project done.

First, look at the queue of projects and sub-projects you are working on. Founders are infamous for having a portfolio of interests and projects– hobbies, side projects, etc. It sounds exciting, until you realize that 1 hour of effort on 20 projects each, will never be able to get the results that 5 hours of effort on 4 projects can, or better yet, that 20 hours of effort on 1 project does.

It’s very likely that you have just the right amount of resources to hit a home run on 1 project, if you focus your efforts. If you narrow the project list down and commit to taking a project through to its full realization, and find you continue to lack sufficient manpower or resources, you may be adding features, functionality, or "side projects" in the main project which are sucking resources away from the core tasks needed to get the job done. We love the concept of "Minimum Viable", and each quarter it becomes a popular buzzword among our founder team– "minimum viable cofounder"… "minimum viable sales process". When you cut down to the least amount possible, taking a minimum viable approach applies what you do have on hand to get mission critical things done, and frees up your time and energy to run the project in a more sane way.

#5. Things aren’t happening fast enough

If founders had their way, things would happen as soon as they thought them up. But in the business world, things don’t happen that way. Major departments take their time making purchasing decisions, customers require 6 or 7 interactions before buying the product, manufacturing requires long intervals of wait time, etc.

When founders are out of resources and the fate of the project is seemingly waiting on critical purchasing or funding decisions to move forward, it becomes imperative that the founder wait it out, if waiting is the necessary element. Sometimes things simply require time, in between steps in the process, and it’s critical for founders to recognize when waiting is the best action step you can take.

#6. Founder burnout.

After a certain level of high stress/low reward interactions or problem scenarios, it’s difficult, if not impossible, to maintain the high-intensity momentum and energy required to make it through the startup phase, after which things calm down and the project stabilizes.

Founders are typically achievement-oriented, workhorse, high-energy people, who can forget their human limitations in pursuit of opportunity and challenge. In just the right quantities, these traits will sustain a project through extremes that make high achievement possible. But without the buffers of down time, rest, and reward, founders are susceptible to burning out, just like anyone else.

Immediate solutions are a day off, vacation time, spending time with friends or family, sleep, and doing activities that are completely unrelated to work.

Long term solutions include decreasing the high-stress operating mode (it’s not actually necessary for getting things done!), bringing on a cofounder, meeting regularly with an advisor who can provide outside perspective, and setting up a work environment in which stress is moderated and burnout is consistently buffered against.

#7. Can’t find a good cofounder.

This problem can seem daunting– a startup project is "your baby", how can you find the right person to trust to share decision-making and control of the project’s future?

That is actually the real problem behind not being able to locate a cofounder– deciding to bring someone on, and being willing to give up complete control of the project’s direction.

There are plenty of talented, skilled people located in your city, or available within your industry. The task at hand is to a) define the role you need filled, b) locate 3-5 potential candidates you are serious about and c) give up enough control of the project, in an incrementally-staged, low-risk/low-commitment hiring process, so that you can bring a heavyweight cofounder on to help share the burden and opportunity of the project.

#8. Too wide a gap between what you currently have, and what you need to move forward.

Entrepreneurship requires getting comfortable with the unknown, with gaps & half-baked ideas and beta versions. It’s up to the founder to look as far down the path as you can visibly see and take action on as many situations as you can based on the resources you have available. Along the way, there are gaps and barriers that present themselves, and things can get uncomfortable.

When you’re staring at a situation that seems unsolvable, and you know clearly that you lack what is needed, you’ve just run into a gap. Here are a few options–

a. Generate alternative options

b. Identify someone who does have the resource or solution necessary, and approach them about a win-win value exchange

c. Ignore the gap for the present, move forward with what you can do until you have the resources or solution required to fill in that space

#9. Struggling to successfully accomplish the variety of tasks needed in the project.

This is a tricky situation– founders are expected to be jack-of-all-trades, willing and able to do any job the business requires, from CEO to janitor, and everything in between.

Yet, as multi-talented as founders are, it’s unlikely that they are good at, or even sufficiently skilled enough, to tackle all of the various departments of the business successfully. There’s a difference between doing something for the first time, and doing it right, and many entrepreneurs fail to perceive this difference.

Maybe you’re good at the technical skills, and can hack your way through finance and marketing collateral, but you completely fail at running a sales process. Unfortunately, the intuitive thing– to increase your skills in that area, or give it the old college try– isn’t necessarily the best option. 

Consider outsourcing things to others– having an intern run your books for you, or partnering with another entrepreneur to trade (I’ll set up your sales process, if you write my marketing content). It’s also likely that your peer entrepreneurs in the startup community are currently struggling with tasks you do well, and vice versa– why not trade tasks until you can bring on more manpower?

#10. Major progress in one or two areas of the project, lacking momentum in other critical areas.

This is related to #9, but different. By default, founders in high-stress scenarios will fall back on their strengths. So for a technical founder, they’re likely to code or work on product development, and to shy away from putting time & effort into the sales or biz dev end of the business. And vice versa for a biz dev founder.

The problem with this situation is that a business that is functioning on all cylinders, requires at least a triad of skills– biz, tech, and project management. Related to biz, the project requires consistently flowing revenue or funds, and constant business development. Related to tech, the project requires iterations, user testing, product development, specs from users regarding what they need/will pay for, etc. And project management requires tracking the time, team, resources, and overall milestones that keep the business above water and delivering value to customers on a regular basis.

If a founder hasn’t yet transitioned from a 1-man show to having a cofounder, or building out a full team, this problem becomes more compounded. The founder is likely to have a lot of progress in product development and almost none in business development. The first thing to do is to take a snapshot of where the project is at across all levels, and even out the pace, so that business development efforts are brought up to a relatively matched level of progress, and to grow the business forward across all categories at the same pace.

The Sum-Up

The interesting thing about entrepreneurship is that it’s such a fuzzy, intangible occupation. Most of the challenges listed above, and the daily grind of getting a business up & running, or getting a product to market, can’t be seen visibly or measured conclusively, and it requires a specialized skillset of relationship abilities, stress/crisis management, team/project management, business savvy, salesmanship, and a huge willingness to experiment and change.

A core need that founders have is to internalize a "playbook" of business, to have a mirror of reality in which they can see themselves and their projects clearly, and to identify landmines and critical decision points as they happen, and safeguard the project from dead end routes.

This is one of the most exciting things about the work we do in Portland Ten– working with founders to navigate through these problem situations more quickly, and to take the simplest, most effective path to launch & grow their projects.

What’s On Queue for Fall 2009

We’re looking forward to the next round of Portland Ten, starting September 21. We’re also excited to announce an open-enrollment, low-commitment, modified version of the full 18 month program, called Six Week Sprint, which you can read more about here.

Both the "10 at $1MM Program", and Six Week Sprint, have been specifically engineered to help founders get results and to make life in a startup a little bit easier. If you find yourself resonating with the challenges above and would enjoy being part of either of our fall teams, it’s not too late to apply– start by filling out the application for the $1MM by 2010 bootcamp here, or register for the Six Week Sprint here.

See you this fall!