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10 Lessons for Bootstrapping Your Startup to $1M Annual Revenue

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In an entrepreneurial landscape dominated by headlines of unicorn startups and billion-dollar acquisitions, getting a company to $1 million in annual recurring revenue (ARR) may sound like small change. Let’s be real, though, hitting $1 million ARR is an aspirational milestone most young companies can relate to. And it’s not that easy, especially if you’ve secured modest investments or no investment at all.

The software-as-a-service (SaaS) company I work for falls in the latter category. We’ve never raised a single investment dollar, and it took us four years to reach the $1 million ARR threshold. It was a wild four years. Frustrating, fun, scary: you name the emotion, and we’ve felt it.

But more than anything, it was an instructive four years. We learned so much, and we want to share a few helpful tidbits with our peers out there in the trenches, scratching and clawing your way to your next big milestone.

Here are 10 things we think are most important that you can use in your own start-up journey:

1. Don’t quit

Steve Jobs famously said that the difference between those who make it and those who don’t is perseverance. At one point I remember hearing “Folks, I don’t know if we’re going to be here next month.”

It’s frightening not to know where you’re going to be next month, but you have to continuously figure out how to get a few more customers and extend your runway. You can’t “make it” or succeed if you don’t exist, so you can’t quit.

2. Give your customers everything

At the company I work for, Text Request, we spent hours with our customers. We built whatever they asked for (if it fit with our goals and other customers could use it too). We also gave away a lot of free software.

If you want to grow and gain customers, you have to create a needed product that solves your target customers’ problems. Determine who your target customers are, ask them what they need, and then tailor your solutions for them.

3. Try everything you can think of

The book Traction by Gabriel Weinberg and Justin Mares covers 19 sales and marketing channels for startups to test. We tried all of them. We went to events. We advertised. We started a referral program.

For us, cold calls and cold emails worked surprisingly well. We took an industry, looked for companies in a given city, and reached out to set up product demos. Organic search has increasingly helped our sales funnel, too.

Either of those could be the best plan for you, or it could be advertising in a particular channel. Every startup is different and targets a different niche, but you’ll only find successful strategies and channels for growth by testing all your options.

4. Focus on the basics

When you focus on doing the basics, opportunities open up. When you commit to SEO basics, your targets will find you online, and a big fish will occasionally swim by. When you provide fantastic customer service, a few users will leave reviews and tell their friends. When you keep your head down and do the work, eventually you’ll look up and have hit a big milestone.

5. Get the right people on your bus

This is one of the critical lessons from Jim Collins’ Good to Great. Thankfully, our small team had the right people from the beginning. Brian and Jamey Elrod, our husband and wife co-founders, had already started a successful company from scratch (Educational Outfitters). Our third co-founder Rob Reagan has created software for twenty years and published a book last year on building apps for global scale.

Rob brought a couple of top-notch developers with him, and the rest of us showed up determined to figure the business out. If you’re going to take a company from $0 to $1 million, every member of your team has to be dedicated to working together for the long-term benefit of the company over self-interest.

“Coming together is a beginning. Keeping together is progress. Working together is success.” – Henry Ford

There’s always something that keeps entrepreneurs up at night, but you can put the questions below to rest:

1. How do you build it fast enough?

In the early days, we worried about losing a customer because we didn’t have [X]. It was stressful knowing that So-and-So would move on to the next option if we couldn’t deliver fast enough, and many times they did. But that doesn’t matter.

Losing one customer isn’t worth pushing out a faulty product. Despite the pervasive Lean Startup mindset, it’s more important to your customers that you create needed features (read: solutions) that work great the first time. They have to trust that you’ll give them the tools they need to accomplish their goals, or they’ll leave.

2. How do you keep customers longer?

Our support is perhaps our #1 competitive advantage. One of the things we’ve learned is that a lower price, and sometimes even new features, won’t keep customers around longer.

To keep your customers from churning, you’ve got to do two things: First, provide a smooth onboarding process that immediately teaches customers how to gain value (solve their problems) with your product. Otherwise, they won’t pick it up, and they’ll eventually leave.

Second, always be there with kind words and helpful content whenever a customer needs help. If you aren’t, they’ll get frustrated and find someone else to help them.

“People do not care how much you know until they know how much you care.” – Teddy Roosevelt

3. How do you get people to your website?

Advertising might be a good option, but if targets aren’t already thinking about what you can do for them, they probably won’t care about your ad or purchase. Instead, create content to educate viewers and help them solve their problems.

Focus on growing your organic traffic, becoming a trustworthy source, and honing your brand’s voice before spending lots of money on ads.

4. Do you need investment money?

When you’re floating in the middle of the ocean, you’ll do anything for a ship to pick you up. But sometimes you just need to swim. We chose to swim, and you might want to do the same.

When every dollar spent has to fight to prove its worth, you’re inevitably going to build something more valuable and more sustainable. Plus, bootstrapping gives you more control over what decisions you do make to grow your company.

5. How do you pursue 10X growth?

A growth hack is not going to propel you from 100 customers to 10,000 overnight. It doesn’t take one trick, but lots of little and big things working together to create exponential growth. It also takes time.

Instead of looking for a golden goose, create complete and actionable strategies. Those, and a little patience, will help you achieve exponential growth.

Growing your startup to $1 million ARR is not easy, but it’s possible – even without investors lining up to give you money. Put the 10 lessons above into practice, and, with a little time and a lot of work, you’ll get there.

Is there a business you’d like to start or have started? Share your ideas and suggestions for our readers!

Startups

8 Key Factors That Discourage Investors From Putting Money Into Your Startup

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Today’s ideas are tomorrow’s winning businesses. Ideas executed brilliantly and with proper investment bring your business success. That is how the world of business got the likes of Apple, Google, McDonald’s, Amazon and so on.

But why in spite of the brilliant and promising ideas at the core of their business, many startups fail to attract investors? Why do investors hesitate to put their money into some startups? Well, investors have reasons and only by deciphering these reasons we could get hold of some deterrent factors that hold them back.

Let us explain some of the vital factors that prevent investors from putting their money in the startups below:

1. Inefficiency or Absence of Leadership Qualities

Inefficiency is the most significant deterrent factor for pulling the success of most startups. This can also be referred to as the lack of leadership qualities. Investors always want to make sure that they don’t lose their money through a company that has an extraordinary business model but no efficient and skilled business leader to make it successful. When fetching investment from investors, you need to offer a clear prospect and detailed plan of how you are going to achieve the goals.

2. Lack of Trustworthiness

An investor puts his money on a venture purely on the basis of the credibility and trustworthiness of the business. This is why besides having a sound business plan with clear objectives, you need to establish the integrity in terms of the security of the investor’s money and how the fund is going to be invested to give results as per business plan.

If an investor has a feeling that the startup may not have enough customers to fulfil its financial liabilities or if it finds that the business is hiding some information, it may further push the trust of the investors down. Total transparency and establishing the faith of the business brand are crucial for finding investors in favor.

3. Lacking Experience in Business Management

You have a great business idea backed up by a sound business plan and solid trustworthiness based on your background, but you have zero experience in managing a business. This is a serious reason for an investor to deny making any investment in your business. An investor cannot put his money just to allow you trying and learning your management skills the harder and riskier way. Uncertainty is the single biggest turn-off factor for any investor and lack of managerial experience is synonymous to that.

4. Business Model is Not Sound Enough

You have a business idea, some efficient, competent and experienced professionals as leaders, the great stamp of trust and pretty much everything that make a company look promising. But what about your business strategy and business model? Are they sound enough to take on the market competition and challenges for business growth? Well, this is what investors are most interested in.

In most cases, a business model is what makes an investor think twice and even take a backward step from investing in a startup. After all, your business model and strategy will decide how your business and products will be able to withstand competition and become victorious.

5. Taking Investors for Granted

This is a big mistake on the part of many startups. Just by becoming confident in the potential and the soundness of the business model and prospect, a business can consider getting investors on board requires just a little effort and time. But in reality, getting investors on board is the toughest thing a business can think of.

This is why without proper and meticulous preparation, it would be foolish to approach investors for your business. Most investors receive hundreds of such emails and a similar number of approaches through other means and they coldly just let them pass. This is why you need to send them very detailed proposals backed by strong recommendations and referrals.

6. Targeting the Wrong Investor

Every business has a target customer base, right? Not all customers are interested in every product in the market. Similarly, not all investors are interested in your business. Investors based on their prior experience and industry exposure, put their money in businesses that they know like their own palm of their hand.

So, targeting an investor who has no interest in your business will only drain your energy and bring you unnecessary frustration. When you are seeking investors for your software startup, don’t approach someone investing in real estate business.

7. Non-Realistic Proposal for Funds

Investors normally come with huge experience of your industry and so they have a clear idea about the fund requirements for your business startup. Moreover, they already have invested in other ventures or have gone through many proposals. Naturally, they have every bit of estimate already in their mind. So, any proposal claiming a lofty and unrealistic amount will only face rejection.

This is why it would be wise to become meticulous about your estimation of the required fund and calculation of various cost factors. Have meticulous details about every facet of investment backed up by breakup of the costs. Only when you can convince them with correct estimation, investors can take interest in discussing the matter further.

8. Make Sure Your Product Solves a Customer Problem

Will any investor put money in building a simple calendar app now? No, simply because such an app idea has no value for the end users now. Will an investor put money in a product that has already been outdated and has no use? No, no investor has to even go through such a proposal for dismissing them.

Well, to fetch investment, your product must be thoroughly customer-centric. It not only has to solve a problem but has to deliver some competitive value in comparison to similar products in the market.

Obviously, finding an investor for a new business is not an easy task, considering the huge competition that businesses need to deal with. But, if your business idea is unique and you fill all those requirements correctly as mentioned above, finding investors may not be as tough as it sounds.

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5 Must Have Branding Tools for Your Startup

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Your brand is more than just the colors on your website. And for startups, it’s important to create a strong and memorable brand from the beginning if you want to stand out from the competition, scale your company, and find your ideal customers faster.

Here are 5 simple tools that will help your company avoid branding mistakes, take charge of your visual identity, and set a solid foundation for future growth:

1. Graphic Design Software

The word “design” doesn’t have to be overwhelming. Before deciding on your startup’s logo, colors, designs, and overall tone, consider working with a brand strategist who can translate the core ingredients of your startup into a visual identity that speaks to your target market.

Brand strategists have expertise in the psychology of colors, shapes, textures, and words, and they will work with you to make sure that your branding appeals to your target audience. Once you have those basics of your brand established, there are several tools that can help your company refresh and maintain your visual identity.

The absolute best graphic design tool for non-designers is Canva. While the free version has a lot of functionality, the paid plans offer more customization such as the ability to import your exact brand fonts and colors.

But if your company handles all of your design in-house, you will need something more advanced than Canva. In that situation, I would recommend Adobe Creative Cloud to startups who work on their designs in-house, as it includes top-notch design software like Photoshop, Illustrator, Lightroom, InDesign, and more.

“Branding is what people say about you when you are not in the room – Jeff Bezos

2. Visuals & Creative Imagery

Have you ever wondered where your competitors get those beautiful branded photographs that end up on their website? While it’s possible that they worked with a photographer, it’s also likely that much of their imagery comes from stock photos.

Here are my recommendations on the exact places to purchase stock imagery to improve your company’s branding:

  • Creative Market – A treasure trove of quality visual imagery where you can buy anything from stock photos, to branding mockups, to social media templates (Facebook cover photo, anyone?), to custom fonts… the options are nearly endless.
  • Adobe Stock – Beloved by designers, and the platform offers tiered pricing plans based on your image needs and download quantity.
  • Pixels – If you’re on a tight budget and just need to grab an image or two for a blog post, you may be able to find what you need on Pixels – which is great because all of the photos and videos on Pixels are free!

3. Social Media Scheduler

You’re a leader. You’re an entrepreneur. Your staff, board, funders, and admirers depend on you to make big decisions, lead the ship, and plot the vision towards your company’s future. You don’t have time to stare at a blank screen every day wondering what to post on Facebook.

By using a social media scheduling tool, you can sit down for a few hours, schedule batches of content, and schedule the dates and times when it will post to your accounts over the next couple of months. Then, once the content is posted, you only need to worry about responding to comments and engaging with your customers. 21st century efficiency at its finest.

Popular social media schedulers include Buffer and Hootsuite, both of which include free and paid plans. Not sure what exactly to post? Check out these social media ideas from influential businesses. And if the idea of writing and planning months of content still overwhelms you, our next tool will help you stay organized and on-brand.

4. Editorial Calendar

When it comes to your content, it’s time to step it up a notch and start thinking like a media outlet. Every piece of content that you put out as a company, whether it’s an e-mail blast, blog post, social media post, podcast, or video, needs to be aligned with your brand.

Each major magazine maintains an editorial calendar which outlines the overarching theme for each of the upcoming 12+ months. By establishing a monthly content theme in advance, they create a framework to generate and organize their ideas.

Consider creating an internal editorial calendar that will guide your startup’s content over the next 6-12 months. The software tool you use to maintain your editorial calendar isn’t that important — I like to use Trello, but you can also create a simple numbered list in Google Docs or Microsoft Excel. You may be surprised at how quickly the creative juices flow once you have an editorial calendar in place.

“Design is the silent ambassador of your brand.” – Paul Rand

5. In-Person Networking

Offline efforts count towards your branding too! And if you run your entire startup from behind your laptop screen, you miss out on ample opportunities to build your business offline and gain local referral partners.

If you’re new to in-person networking, start by visiting Meetup.com or Eventbrite.com where you can browse for events in your area. Think outside the box when it comes to selecting events to attend. For example: If you’re a chiropractor, it makes sense to attend local holistic health meetups. But you could also attend a travel event and meet digital nomads who don’t yet realize that a chiropractor can help them recover after long plane rides.

Remember that you’re not at the networking event to make instant sales, you’re looking for referral partners and connections. Don’t be the person who tries to shove your sales pitch down everyone’s throat upon meeting them.

As you can see, there are many simple online and offline resources that can help you spruce up your branding, reach new customers, and pique the interest of your target market. If you take branding one step at a time and start with the tools above, you will be well on your way to creating a brand that your customers will cherish and remember.

Have you used any of these branding tools before? Are there any additional tools that have helped your startup’s branding shine? Share your thoughts below!

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5 Ways to Deal With Startup Uncertainty

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Starting your own company may sound like a dream come true in your mind, on social media, and to all the people looking on in envy from their office jobs. But when the fantasy fades, you realize how much uncertainty you now have in your life. The inherent risk in any startup is that you are trading the certainty of a normal job for real growth and freedom. What people get from office jobs is much more than a steady pay check and free coffee. It’s a sense of certainty that their lives, work, and finances are in order.

You will have to give up certainty to fully take on the risks of this lifestyle. It will be roller-coaster and something you need to prepare for. Logically, it’s easy to know that. But emotionally, there are so many ups and downs in an entrepreneur’s life. Stress, frustration, and decreased motivation are inevitable.

Here are 5 ways you can deal with startup uncertainty:

1. Stick to a morning routine

There’s many ways to start a morning routine. What’s important is to have a stable, predictable routine. This centers your mind and gives you some order to your day. You manage your business and you can do whatever you want. No boss and no one telling you what to do, it can be mix of productive to outright messy days. By giving yourself some stability, you start the day off in a predictable way so that you can jump into work each day.

It’s as easy as taking your dog to the park, having a cup of coffee, and listening to a motivating audiobook for 20 minutes. You may need meditation to get into the state. Whatever it is that you need to get from a sleepy/hungover mindset to that of taking on the day.

“If you win the morning, you win the day.” – Tim Ferriss

2. Make time for high performance books

Speaking of audiobooks, everyone – especially entrepreneurs, need motivation. Get a few motivating books from other business leaders. This will do incredible things for your mindset and the way you think. Most of them help by keeping you excited for bigger goals. Look for classics from Jim Rohn and Tony Robbins. Or the newer motivational personalities like David Goggins and Rachel Hollis. You’ll be surprised at how much hearing someone’s hardships on their journey will help you on your own.

3. Schedule your week

It’s easy to get a packed calendar working an office job. Everyone else in the company seems to be demanding your time for one meeting or another. Pointless meetings are even the reason some people leave their jobs in the first place. The issue with having your own startup is that while the pointless meetings are gone, so too is any semblance of structure from a filled up calendar.

Spend one evening and fill the upcoming week as much as possible. I recommend Sunday afternoons to think about your goals. Plan big tasks every day throughout the week. That way you always know what you should be working on and stay on track.

4. Hit the gym

This one is actually part of my morning routine and it’s benefits can’t be overstated. Exercise helps fight off anxiety and stress. There’s no better way to funnel your business frustrations more than into the weights. By the time you’re done, your body and mind will be much more relaxed. A necessity when it comes to the tension of being an entrepreneur. Whether that’s staring at your laptop or making sales calls.

“Daily exercise is an insurance policy for future illness.” – Robin Sharma

5. Be grateful

Gratitude was one of the feel good things that I always used to skip whenever it was mentioned. I wanted cold, calculated strategy or tools I could use to build a business as fast as possible. Many brilliant minds in not only self help but also in business, speak about the need for gratitude.

Here’s why it helps me when the business is going through growing pains or everything seems like it is going wrong. I get filled with doubt and uncertainty and gratitude is the quickest way to relief.

Yes, starting your own business is a massive effort, but there is always some job out there. You decided to launch something of your own because you don’t want a baseline existence. You want to grow and build with the freedom someone can only give themselves.

That alone is enough to be grateful. But if you need more, how about that most people are too scared to do what you’re doing. Or that you are taking the time to believe in yourself and live a life of taking chances.

That speaks to your character and self-worth. Much more than the life of quiet misery so many people in the world allow to decide their entire lifestyle. Be grateful you have this opportunity and make the most of it.

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The Best Side Hustle You Can Start Today In Just 15 Minutes

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The best side hustle you can start in 15 minutes is blogging.

It can be writing, making videos or speaking about topics you love through a regular podcast show. All of these acts are a form of blogging.


15 minutes is not long

That’s why blogging is a good choice.

A video that’s less than 15 minutes is easy to make and will work well.

A short piece of writing can be written in under 15 minutes.

A 10-minute audio conversation on one single question will give people heaps of value and detail in one particular area.

Starting is not where the power lies. Doing this side hustle every single day is how you get what you’re really looking for.


Many successful people are doing this

Whether it’s Hollywood actors like Will Smith or writers like Tim Ferriss or musicians like Ariana Grande — everyone is doing it.

Why is everyone doing the side hustle of blogging?

  1. It’s how we connect with each other.
  2. It actually works.
  3. It’s a way to create an audience which can become a business.

I didn’t invent this side hustle

I just tried it for myself and saw how powerful it was.

It got me:

  • New clients for my 9–5
  • A new 4 day a week day job
  • Clients to coach via Skype
  • Features in major publications like CNBC
  • The opportunity to meet amazing human beings like LinkedIn influencer Michael Chapman

The side hustle of blogging gave me meaning for my life

Before this side hustle, I was washed up, uninspired, negative and pissed off with the world.

Spending 15 minutes to start the habit of blogging got me out of my head. It forced me to search all over the internet and find things to talk about. Pretty soon I was spending 2+ hours a night researching personal development and figuring out what I wanted to blog about.

Blogging led me to want to help the homeless, share my very private battle with mental illness, come to grips with my startup failures and share the lessons, and even overcome my fear of public speaking in the process.

Now I have a meaning for my life thanks to the side hustle of blogging. I reckon it can do the same to help you grow and get you to the next level. You can blog about whatever you want and then watch it grow from there.


Why is blogging the best side hustle?

It’s how you be creative.
It’s how you express yourself.
It’s how you grow.
It’s how you attract the right people into your life.

There are many side hustles you could choose. Blogging is one of many. In my opinion and based on my experience, it’s the best. There are so many avenues you can go down.

Attracting what you want in your life has a lot to do with what you’re putting out into the world”

Blogging is a fantastic way to put out more of what’s important to you, into the world. Like a magnet, blogging attracts more of what you put out into your life.


Oh and don’t forget the income

Investing, giving back and making an income are all possible through blogging too. Part of my monthly income comes from blogging.

This allows me to back causes that help those in need, invest in stocks that provide me with a passive income and have money to spend on the occasional treat such as dinner dates and drinks with my co-workers.

That money comes from:

  1. Ghostwriting for other people
  2. Posting on Medium.com
  3. Coaching clients via Skype
  4. Consulting to businesses on how they can create content that aligns with their brand

There aren’t too many side hustles that can do that for you

Seriously, blogging is a game-changer. It’s a habit you can start in 15 minutes and repeat daily without much effort. Choose your poison — writing, video or audio — and then get started.

Do it for around twelve months and then send me an email with what you experience. I already know, having challenged lots of people already to start this side hustle, that it will work. It just requires patience and the habit of doing it daily.

15 minutes to start today.

And then 15 minutes every day for the rest of your life.

Try it.

<<<>>>

If you want to increase your productivity and learn some more valuable life hacks, then join my private mailing list on timdenning.net

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