Kris KelsoLeadership Coach | Author | Keynote Speaker

Author of "Overcoming The Impostor: Silence Your Inner Critic and Lead with Confidence". Co-Founder of several companies. Executive Coach to entrepreneurs and their leadership teams. Advisor at the Nashville Entrepreneur Center. Keynote Speaker. Professional Certified Coach (PCC).

Recent Answers

After founding one company on my own, and co-founding several others with teams, I've written and spoken extensively on this topic - it's an under-recognized risk and challenge of entrepreneurship. You can read one of my more popular articles at, but I'll summarize it here...

Entrepreneurship can be a very lonely endeavor. Even when you have others on your team, no one else is in quite the same "boat" that you are.

Looking to other entrepreneurs for support can be deceptive. Most entrepreneurs are always "on" - showing only the best side of their business - and it's easy to understand why. As an entrepreneur, you're constantly selling yourself and your company to potential customers, employees, and investors. As a result, you compare yourself with others who are only showing their best side (and only sharing the good news), while you know that your own pursuit is a daily struggle.

Raising money (if you are going that route) is an exercise in perpetual rejection. It's a real test of your self confidence to be told over and over why your idea won't work and isn't worth an investment. If you're not raising money, you may deal with this same challenge when trying to find your initial customers or employees.

I've found three primary ways to counteract these forces and stabilize my own perspective:

1. Find some peer entrepreneurs with whom you can build some truly deep and transparent relationships, where the masks come off. Share your insecurities and vulnerabilities with them, and allow them to do the same.

2. Find mentors, advisors, and coaches who have experienced the same ups-and-downs you are facing. Listen to their stories, soak up their wisdom, and most of all, realize and remind yourself that they survived it, and so can you.

3. Recalibrate your perspective by taking time off to help others who are less fortunate than you are. Volunteer with an organization that supports a cause that you care about. The side effect of focusing on others is that you will be reminded that the challenges you are facing are not the worst problems in the world.

Finding a coach is easy - there are many of them out there. Finding the right coach is the challenge. There are several factors to consider:

Working with a coach that has similar experience in their background is not absolutely necessary, but can be very valuable. Having someone that can truly understand what you're trying to accomplish, and can empathize with the challenges you face, will help smooth communication.

Coaching skills are equally important, though. Many experienced business people position themselves as "coaches", but they aren't actually very skilled at coaching - they're more likely to tell you what *they* would do, rather than truly help you dig deep and find the right answer for yourself. The result is that you end up pursuing your version of someone else's goal, or someone else's version of your goal. Neither is totally fulfilling.

"Fit" is also really important. Personality, communication style, sense of humor... - these all factor in to the quality of a coaching relationship, and are very personal and unique to each coach. Take the time to meet several potential coaches and see who you connect with. Also, don't ever feel bad about saying "this just isn't working".

I used to be very skeptical of coaching as a profession, for a number of reasons. Once I found the right coach, though, the experience was transformational for me, and pivotal to my success as an entrepreneur.

I'd be happy to have a conversation to determine if there's a "fit". I work with dozens of entrepreneurs, having been one myself for over 12 years. I'm not right for everyone, though. You have to make that determination for yourself.

I've done both - founding a consulting firm, which is now 10 years old, and having co-founded a technology company (Healthcare Blocks - a PaaS for the healthcare industry). There are many, many ways in which these two business models are almost exactly opposite of one another:

The consulting firm has a handful of clients each year, with many contracts for six-figure dollar amounts. The technology company has many more customers, but the revenue per customer is lower.

The consulting firm has almost no recurring revenue (it's all project-based engagements that have a scope and an end date), whereas the technology company is almost all recurring revenue (subscription services) that is expected to go on indefinitely (there's no set end date at the beginning of the relationship).

The consulting firm was built largely on relationships, referrals, and word-of-mouth reputation, with almost zero spent on marketing and advertising. The technology company was built with on-line advertising, data-driven customer acquisition, paid referrals, channel partners, etc.

There are also differences in the flexibility afforded, the people you have to hire (or contract), and the capital required (I built the consulting firm with my own money, but raised some investor capital for the technology company).

As has already been said, you can start with one and look for opportunities to do the other. In fact, many consulting / services companies eventually try to build a product of some kind, to gain the stability of recurring and (somewhat) passive revenue. However, they don't always realize that these are two very different business models that have to be approached differently, so this kind of transformation fails more often than it succeeds (of course, more than half of startups fail anyway, so I suppose that's to be expected).

I have advised and helped dozens (maybe hundreds) of entrepreneurs in both business models. If you are interested, I would be happy to talk through some of these differences with you, and even learn more about your personality and preferences to help you determine which you might enjoy more. Let me know if that is of interest.

This is tough to answer without knowing more about you. What skills, resources, and relationships do you have at your disposal?

One of the simplest businesses to start is a consulting practice. However, "immediately" generating income will depend heavily on what sort of relationships / contacts you already have, and how great the need is for your particular expertise.

Since all I know about you so far is that you've been involved in a startup, I'd recommend you look to your local startup / entrepreneurship community to find another company who needs some short-term work you could do on an hourly basis. You've apparently got surplus time, so monetize that while you figure out what's next.

I've run multiple businesses while leading a family, maintaining friendships, working with non-profit organizations (I sit on several boards), and being an active leader in my church. It's certainly not always easy, but it's rewarding when you can maintain the right balance.

Here are a few tips:

1. If something is important to you, put it on your calendar. This includes family time, friendships, rest and relaxation, etc. I have found that if something doesn't get from my to-do list to my schedule, it often doesn't get done. This applies not only to work items, but to personal ones as well.

2. Create some space away from your work. Set time-based and geographic barriers for yourself (i.e. no working in certain rooms in the house or after a certain time at night). Create some rules and stick to them - even find ways to reward yourself for sticking to your boundaries.

3. Recognize that you get diminishing returns after a certain point. If you are working a ton of hours and shortchanging yourself on rest and recharging, you will eventually get less productivity and lower quality work out of yourself. That means you'll have to work 80 hours to get the same output you used to get from 50 hours, and it becomes a vicious cycle. If you look at the time away from your work (especially sleep) as an investment in the quality of your time at work, you can do more with less.

4. Recognize the value of your relationships. When I'm struggling with stress at work, it's great to have a supportive wife and encouraging friends to help me maintain perspective, and to remind me what is important and what I'm capable of. But those relationships can't be built in the moment you need them - they take time to create and nurture. The saying "dig your well before you're thirsty" applies not only to business relationships, but to personal ones as well.

A couple of years ago, I gave a talk on this topic at a leadership conference. You can view the video (about 13 minutes) here:

I hope that's helpful!

I've seen this model a lot lately (not a criticism, just a fact). The internet has certainly created plenty of opportunity to bring buyers and sellers of a particular product together and create an efficient marketplace. What you have, though, is a classic chicken-and-egg problem. You need buyers to attract sellers, and you need the sellers to attract buyers.

Without knowing the actual market / product, it's difficult to give much advice, but one thing that I've seen help in this scenario is to take your market, and further slice it into niches, and focus on one niche to begin with. This gives you a couple of advantages:

1. It allows you to get hyper-focused on who your customer is, making introductions / referrals easier. This is counter-intuitive, but the more narrow your focus, the more likely you are to get other people to understand what you are looking for and send prospects your way.

2. It allows you to get maximum bang-for-buck in advertising and marketing, because your audience is more narrow and easy to identify. You can also target specialized trade shows or other, similar marketplaces where that audience can be reached (again, I don't know any detail about your business, so I'm generalizing).

3. It allows you to refine the MVP with a very narrow audience before opening it up to a wider group after it's been proven. You may find that changes are needed in order to widen your audience / customer base, but that's OK - you've proven that the model works and is worth investing in further.

I would be glad to discuss your model in detail and give you some more specific examples of what I've seen work if you are interested in scheduling a call.

I am an entrepreneur without a single degree or certification to my name. I'm certainly not anti-education (in fact, I've taught some university classes), but higher education wasn't the path I chose.

My question for you is: what type of learner are you? I learn best when I'm self-directed, studying things that fascinate me, and able to either apply or teach what I'm learning (in fact, I think teaching is one of the best ways to learn). So, I've taken ownership of my "education", and I am constantly learning. I read books and articles, listen to podcasts and other audio programs, attend conferences and events, and seek mentors and peer-learning environments.

It has worked well for me, but not everyone is built that way. Some people learn better when the education is structured for them, or when they have schedules, deadlines, and feedback (i.e. grades) on their learning.

Even for structured learning, college / university is not the only option. There are incubator / accelerator programs, entrepreneur boot camps, mentoring groups such as SCORE - some of it depends on where you are located, or whether you're willing to travel.

The bottom line is that education is not optional (especially for an entrepreneur), but there are several ways to get an education. You need to figure out what kind of learner you are to determine what path (or combination of paths) you should take.

I am a member of several startup and early-stage company advisory boards. As with many areas of life and business, there are not strict guidelines or standards, and the arrangements can vary widely. Factors include the type of company (and perceived potential value of the equity), the experience and / or prominence of the advisors (i.e. are they just bringing knowledge / expertise, or do they also add "clout" and open up a lot of doors?), and how early in the company a particular advisor gets involved.

However, a lot of "typical" deals for early stage companies involve .5% to 1% of equity (which vests over a year or two) in exchange for 2-5 hours a month of involvement over that period.

Many of the companies I've advised have come out of a startup accelerator program, which sets the structure of the advisor-for-equity relationship. In those cases, the entrepreneurs are giving up a total of 6% of their equity to both go through the accelerator (which also includes some seed funding) and to come out with a small board of advisors.

I've served as an advisor to a number of startups, both in formal accelerator / incubator programs, and on the advisory boards you are describing (not to mention the free advice for friends and family).

It sounds like you've already decided that you want to do it, and you're just looking for potential red flags or pitfalls, so I'll skip the pitch on how rewarding it can be, even if it doesn't "pay off".

Factors to consider:
1. Companies pivot. Founders rarely do. Focus more on the who than the what, because the idea and model might change drastically over time. It's important to like and trust the people you'll be working with.

2. How do you fit with the rest of the advisory board, and is that important? Some entrepreneurs like their advisors to meet and work as a group, while others deal with their advisors very independently. Know what style and what type of team you're signing on to.

Questions to Ask:
1. "What do you expect from an advisor?" You'll get a lot of different answers from different entrepreneurs - make sure your expectations are aligned. Talk about the important things like honesty and accountability, as well as the potential frustrations like responsiveness and scheduling expectations.

2. "What skills / knowledge / experience are you looking for in me specifically?" I might think I have a great marketing mind, but if the board of advisors already has a marketing expert, they may only be looking for my technical knowledge or relationships. Make sure you don't think you're bringing something to the table that isn't what they're looking for.

Lastly, in terms of the deal structure, be honest if they make an offer that you feel undervalues your time and / or experience. Steer the conversation toward opportunity cost (If I commit to you, I have to say "no" to other things that require my time) - that simultaneously demonstrates that you know your value and that you intend to abide by your commitments.

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