My 9 biggest mistakes thus far

The past few weeks, I battled bouts of recurring self-doubt and lack of motivation. It comes and goes. It’s not fun to wallow, but an unforeseen fortuity to self-doubt is introspection. I made countless mistakes in my startup journey thus far. Here are my 9 biggest mistakes, in the order in which I realized they were mistakes.

The 9 mistakes

1. Getting distracted with part-time consulting

Last November, I met a technical cofounder who wanted me to be his startup’s first hire. I respect the guy’s accomplishments and found the mission and domain extremely interesting. I considered even quitting my startup attempt to join his venture. However, I had just started my startup attempt and wouldn’t prioritize his project over my own. I tried to make it work with part-time consulting, but that turned out to be a waste of time for both of us.

Part-time consulting is tricky because oftentimes your client would rather you be full-time. No client prefers their consultants work at partial capacity for them. If you have a part-time consulting agreement, you must anticipate that the client will want a larger time commitment from you.

More importantly, part-time consulting was a huge hit to my own productivity. I worked only 8 total hours for only one week for him. However, my time outside of those 8 hours were spent unproductively trying to push my projects forward but going nowhere.

Consulting was interesting because it was my first time working as a freelancer. I made the classic charge-way-too-little mistake. I’m glad I had the experience, but I wouldn’t do part-time consulting again. That’s just a suboptimal agreement for my client and a distraction for myself.

2. Paying for coworking space

I signed up for a hot desk at Wework Labs in Soho, New York. My intention was to meet potential customers. If that actually happened, then the Wework membership fee would have paid itself many times over. However, it did not. It was just a waste of time and money. I ended up learning that I was more comfortable working from my kitchen table anyway.

3. Not realizing that B2B market validation takes forever

B2B market validation and customer development is a long, arduous process. The entire process is asynchronous. You’re always waiting for people to reply to you. Meanwhile, you fill the rest of your time doing things which aren’t important.

If you’re trying to be a lean startup, you should know that everything starts with knowing your market and knowing the problems you’re trying to solve. You might as well still be employed while you’re validating markets and meeting customers.

4. Thinking I can just “talk to people about their problems”

“Talk to people about their problems” is spouted endlessly by startup pundits. I cheated on B2B with B2C for a few days and can personally vouch for this tactic’s effectiveness within B2C. B2B is not the same. No SMB or enterprise customer will sit down with you and have an open conversation about their problems with you.

The reason is credibility. B2B customers are short on time. To earn their time, you need credibility gained either through fame or having an existing solution. In B2C, it’s sexy to say you’ve earned money before writing a single line of code. I doubt this is possible for most B2B SaaS problem spaces. If you’re not famous like the rest of us, you won’t get any meaningful conversations to validate your market without putting more of your own skin in the game.

5. Allowing myself to be disenchanted with employment

I always knew I wanted to start a company. However, my original plan was to start up in a few years rather than right now. My sudden change in plans happened because I hated my last job so much. I was working for idiots, and I figured, if they can start and run a company, so can I. I couldn’t not try to start up. As my girlfriend put it, I had to do it for my soul.

Months later, when I realized that I could be employed while validating B2B markets and doing customer development, I learned that the biggest error I made was not leaving my last job the very moment I hated my job. Instead, I stayed an extra 5 months, which turned my general dissatisfaction with my employer into a livid disdain for the entire concept of employment.

If you have startup aspirations, I’d encourage you always leave employment as an option. So much work can be done while employed. Employment can also help further your own startup attempt. If you hate your job, it’s probably not employment’s fault, just your particular employer’s fault. It’s not you or employment. It’s your boss. Find a new boss.

6. Not knowing how to cold email

The cold email is an essential skill for B2B market validation and customer development. You can’t get around it. Yes, it’s easier to work your network, but your network won’t be big enough if you’re not famous. The cold email is just as technical as writing code. It requires just as much calculation and problem solving. However, consider the feedback loops of both. With code, you typically get feedback instantly. With cold emails, your feedback loop is as long as it takes for the other person to reply, which could be a week.

Back in the day, when computers were primitive and feedback cycles were longer, code needed to be more accurate. Longer feedback cycles with older computers means more incentive to make each cycle higher quality. Cold email is the same. The lengthy feedback loop means you need to be proportionately more effective to justify the higher cost of waiting.

7. Not enough knowledge of how B2B works

I have a whole host of mistakes which eventually taught me that B2B is just really really complicated.

For instance, I learned that not all B2B customers care about making more money. I dichotomize B2B customers by describing them as either centripetal or centrifugal. The centripetal customers are the ones which are trying to grow their businesses at all times. The centrifugal customers don’t care about making money or having great customer experiences. That’s why they’ve gone for decades with shitty websites.

Another example is the emphasis on a certain ROI. Some businesses care about minimizing costs, but all businesses care about minimizing risk. They want no uncertainties. They want to know exactly how much your product will cost and how much money or time it makes or saves for them. No nebulous benefits like comfort and luxury. Only a hard-defined ROI. It’s the same reason that clients to freelance developers typically prefer a fixed-point bid over time and materials.

Another example is the multiple stakeholders at a B2B customer. Some people say there’s an end user concerned with your product’s usefulness, an IT stakeholder concerned with technical implications to integrating your solution, and a financial stakeholder challenging your ROI story. Only until you satisfy all three of their concerns can you make the sale.

Cold emailing is just one technical skill needed to survive in B2B, which as a whole is more complex than most software that I’ve seen.

8. No domain expertise

Most B2B success stories are led by characters with meaningful domain expertise and connections. Domain expertise means knowledge of the market and credibility. Connections means distribution. All of these are highly valuable and prerequisites to starting up successfully.

I had no domain expertise when I started. Over time, I built up my own domain expertise, but as of now I’m not sure it’s enough. It would have been better if I started on Day 1 already with domain expertise.

9. Creating pressure for me to build and earn revenue asap

By having no source of income, I found myself settling for partially validated markets and products. To be truly successful, I’d have to niche down and validate specific, not broad, markets and products. However, that took time and patience that I often didn’t have.

This is another reason why employment should always be an option. It prevents you from jumping the gun and going all-in prematurely.

People always say that it’s difficult to get yourself to leave your job and take the plunge into entrepreneurship. You should just get over your fear and just do it. This is probably mostly good advice, but definitely not entirely good. On the one hand, the strain of a day job makes it difficult to work extra to validate a market. On the other hand, the day job’s comfort also gives you the patience to take a full plunge only when you’re certain of your market.

If I could do it differently

If I could do it differently, there are a small number of huge points that I’d reconsider:

Protect my happiness to be employed

Most people are employed out of necessity, not choice. If you have the courage to take a full plunge to start up, you probably don’t consider yourself part of this group. Employment can occasionally be a real drag, but it has substantial benefits which could enable your startup attempt. I’d say my previous aversion to employment sometimes boosted my startup attempt and usually hindered it.

In the future, if I sense myself feeling dissatisfied with an employer, I’ll leave immediately.

Validate a market niche while earning a salary

B2B market validation can take a long time. Invalidating a market is more likely to happen than validating it, and invalidation can take just as long as validation. You could possibly be looking for a market for years. Save your runway for execution, not searching.

If you enjoyed this post or would like to give me any feedback at all, I'd love to hear from you! You can tweet me at @dillonforrest or email me at It'd make me super happy to hear from you!