August 26, 2020 – Social Media AI Woofy Arjun Rai and Scale and Abundance Andrea Freeman

August 26, 2020 – Social Media AI Woofy Arjun Rai and Scale and Abundance Andrea Freeman

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Arjun Rai – Founder/CEO of and – Read interview highlights here

We have always been of the mindset that we want to rebuild the
business every 30 days. If you are a competitor of ours, watch out!

Arjun Rai is a New York City based entrepreneur on a mission to support small businesses with the power of visualized data science for digital marketing. He is a 4x serial entrepreneur and investor who launched several startups including,, TheBizDen, and After spending a few years and learning the ins and outs of running a venture-backed startup, Rai set out to modernize another industry related to his former passion of social media. Rai has created HelloWoofy: the only social media management platform to use a real-time auto-complete interface that is affordable for businesses, freelancers, and influencers all around the globe, no matter their socioeconomic background. Arjun also holds several notable awards and is a member of the Phi Eta Sigma Honor Society and Golden Key International Honour Society. He was recently featured on Season 3 of Meet the Drapers, where billionaire venture capitalist, Tim Draper, invested in Woofy.

Andrea Freeman – Mindful Business and Leadership Development Coach

‘Money doesn’t grow on trees,’ and ‘You have to work really hard for it,’ aren’t necessarily true and we can choose to create a new narrative.

Andrea Freeman is a a mindful business coach and peak performance planner on a mission to help service-based business owners realign with their purpose, create greater financial freedom, fulfillment, and make a difference in the world. She operates from the foundational principle that businesses develop alongside the individuals who run them. Andrea started her first business when she was 12, second business at 26, and third business at 31. Professionally trained as an educator and leadership development coach, she honed her entrepreneurial skills and scaled her celebrity event planning business to multiple six-figures in annual revenue. Andrea believes her superpower is seeing people for who they truly are at their core, infinitely powerful, and giving them the tools to access that power and maintain that self-image effectively and consistently.

Highlights from Arjun’s Interview

So let’s start with what’s so special about Woofy, the real-time autocomplete interface. I’m sure you can relate to this. If you wanted to do a chore and you had something else going on; you need to take a sales call, you need to talk to your lawyer, you need to talk to your accountant, who wants to do chores when you need to run your business? Well, similarly, as many of you can relate, small business owners have to do things that they don’t want to do, which is a lot of grunt work. Even if there’s the essence of fun in the the work itself, when it comes to social media marketing or when it comes to content marketing, when it comes to even thinking about social media as a lead generation avenue for their business, it requires a lot of grunt work.

So the autocomplete technology we have developed literally automatically types content for you as soon as you start typing, it gives you recommendations for the best words, the best sentences. On top of that, based on hundreds of millions of conversations we already know based on the engagement data and what has worked really well, we give you the recommendations for the best emojis. Now, you may laugh at this, but believe it or not, according to Adobe’s emoji trend report; don’t take my opinion on it, take Adobe’s opinion, it shows anywhere from 44-64% uplift in engagement and also purchase intent. People are willing to trust the brand or the influencer or whoever is using emojis. Now, of course, you want to be limited in your use, you don’t want to use too much. But if you do use emojis, according to studies, they drive a significant uplift in engagement.

So anyway, all of these things that you have to do, we call it grunt work. This feature allows you to focus on the storytelling, the creative aspects of actually getting the message across. So when it comes to digital marketing, whether it’s content-driven, social-driven, we do all the grunt work for you, so you can focus on the essence of your brand.

We also just recently announced that we’re integrating Woofy with Hootsuite. The partnership actually allows existing Hootsuite users and their nearly 18 or 19 million social media professionals around the world. So for an extra $4 a month, you get all the artificial intelligence, all the data science, all the storage, and also a Google Chrome extension that actually does the autocomplete anywhere on the internet. So imagine typing on a blog post in Medium, on WordPress, typing an email in your favorite email client, taking notes in Evernote. The Chrome extension works literally anywhere for an extra $4 a month.

Now if there’s a certain style you type with, the artificial intelligence will start learning from you and try to mimic that articulation when it comes to suggesting new words, new pieces of content, even the content that’s being discovered for you. So it’s pushing content to you and saying, based on your pattern of posting, we think that you might like this article from TechCrunch, this article from Panda daily, whatever that may be. It’s going to start tailoring the recommendations to your tastes and mimicking your way of writing too.

But keep this in mind, we’re not replacing the human element. We believe that pure automation is actually not beneficial, we want to be an augmentation to the small business owner. We don’t believe that the small business owner has to build a Facebook to have Facebook-like advantages, we don’t believe they need to build the office, they need to go rent an office, they need to have someone else build the office. We don’t build everything by ourselves, that’s the benefit of having technology. In our case, we let you focus on what you do really well which is running your business, and let the artificial intelligence do its part. Just like your best friend, your dog, Woofy takes care of all of that.

There’s a lot of lessons to be learned for a younger origin. I have learned everything from making sure that you don’t hire your friend, just because investors were co-founders, that is a bad decision. I ended up having to fire my friend because of clashes and culture and just because he wasn’t very experienced. So that’s something to take away is don’t hire under pressure, hire because you need someone to take over something and assist you and be the Yin to your Yang. We started a couple of years ago, we had about $12,000 left in the bank after had to letting go. So we had to go into a turnaround strategy where basically I said specifically, “We’re going to make this business work, no matter what, we’re going to turn the company around, we’re going to shift product, we’re going to generate revenue.” I ended up taking a full-time gig at another company, working on the business in the mornings, in the evening, late at night. I put in about $170,000 on credit cards, the salary, my savings, all into the business.

I’m very proud to say, as of about seven months ago, we launched the product. We are now helping small businesses all over the country and all over the world to the tune of 5,000 big businesses, we call them winners. We generated nearly $160,000 in revenue in a very short period of time. We used to see about 3,000 to 4,000 API calls a day, which is basically every time you ask for a word or an emoji recommendation as you’re typing, that’s one call. It used to be about 4,000 a day, we see about 200,000 a day today. So it’s a story of persistence, it’s a story of relentlessness when it comes to believing in something and believing in it so much that you want to see it exist because other businesses need a tool like this. Because here’s the fact of the matter, if you don’t have affordable digital marketing solutions at your fingertips for the price of a cup of coffee, the smallest of small businesses who are really affected today with COVID-19, they don’t have any sense of hope when it comes to competing with the largest unlimited marketing budgets of the world. For the first time with a categorically new tool, a tool like HelloWoofy, we’re giving them that hope back.

We had a $175,000 negative balance including the credit card, so that includes all the payroll I added from the full-time job, all of it went into the business, the credit card lines maxed out, a few thousand dollars ahead in savings all gone into there, and actually my girlfriend pitched in as well with some cash. So the point is, we believe in supporting small businesses so much that we went all in. We had a vision and we made it work. Actually, we’ve always been in the mindset that we want to rebuild the business every 30 days. If you’re a competitor of ours and you consider yourself a competitor, watch out because we’re rebuilding our business every 30 days. So what that means is we’re producing technology that is five to six years ahead, for small businesses who don’t have any other solutions available, and thanks to HelloWoofy, there is available now.

So just as an example, if you have an Amazon Alexa in your home or in your office, here’s what happened to Amazon Alexa as an industry. In the last four months, the smart speaker marketing industry has grown by a whopping 82%. Why? Because people are stuck at home. They’re wanting to consume content, they’re wanting to see their content on their Fire TV through the speaker, they want to get all the Amazon, CNN, and all of the briefings. But what if we could allow you as a small business owner to directly schedule content into the living rooms of your followers, your biggest fans, your customers?

So get this! In the next two weeks, we’re going to be introducing the world’s first Amazon Alexa Scheduler for anyone to become a broadcaster, to directly schedule content; whether it’s video or audio or text-to-audio, it doesn’t matter. We are building that technology for the mom and pop store down the block, for the podcast owner who’s just getting started, for someone who’s successful in broadcasting already, we’re able to amplify your efforts. In a situation where people are stuck at home, you don’t have to pray that they see your tweets or your Facebook posts, you can directly be in front of them in their living room for the price of a cup of coffee.

I also want to go through the marketing part and the first customer piece of the story. If you go to our Facebook group, Content Masters by HelloWoofy, you’ll see a lot of our customers love sharing dog photos, we just have a community of loyal and passionate dog lovers who happen to be customers as well. So the name reference comes from that, where like your best friend, it’s always there teaching you when, how, and what to post. But the idea really came from running several other ventures since I was a teenager. I did an agency in college, did another venture-backed company in college as well.

The frustrating part was, social media for the longest time has been a lot of grunt work. Forget the grunt work part, it also doesn’t look really sexy, it doesn’t look very creative. For a creative individual like me, that was hired to come up with creative content, creative graphics, and storytelling for social media marketing for other clients, using a blunt knife when I’m trying to cook a really viral or really interesting storyline for my clients doesn’t work out really well. So the frustration came from that and I basically said, we’re going to have to build something that is mobile-first, and allows influencers to schedule content, to drive content engagement on their phones, anytime they’re traveling, they’re Uber-ing and what not. So actually, our first version was a mobile app. After $10,000 downloads nearly, we figured out that almost all of our customers wanted a desktop version. So we got into an accelerator program and we pivoted to a desktop version.

Here’s the thing about why people want desktops. People want a bigger screen size when it comes to seeing their marketing trends, and seeing where the content is going, seeing the responses in terms of the engagement itself. While Robinhood is great for trading on your phone, if you really talk to a power user in terms of a financial trader, they’ll tell you they need their at least 12 inches of screen size, to be able to see the market and where they’re going. So I actually was inspired by Robinhood, I was inspired by Ship which was logistics on your mobile phone. You took a photograph and you had a guy show up and pack it for you; we were very inspired by that. But the fact of the matter is, our customers told us, no, we want desktop first.

So anyway, we got into the accelerator, we started building out the desktop version. We quickly figured out that the introductions that were being sent our way were actually bad introductions, and we ended up hiring the wrong kinds of people. Another lesson to be learned there, you must vet the engineers you end up hiring, you need to vet them with other engineer friends that you trust. We didn’t do any of it and ended up costing the company some capital. But that’s fine, we learned from that. We pivoted from that, again, from a cultural standpoint. With $12,000 left in the bank, that was the part of the story that I was telling earlier, we decided to turn the company around, hire brand new developers offshore, and the rest is just history.

Now, the first customer, about seven months ago, we ended up launching with AppSumo. Now one of the things I’ll tell you is, channel partnerships are incredibly important even before you launch your first product. Because what that allows you to do is not have to focus on finding the customers that would be in your demographic and the persona that you’re looking for. If you partner with someone that already has the demographics and the personas that you’re looking for, in our case, the smallest of small businesses, AppSumo was able to help us find that. So within about 30 days, we had a few thousand dollars worth of revenue already booked and going into 2020. Then we ended that partnership and it continued with our own sales after that.

Today, we’ve generated a lot of revenue on our own because we were able to use Facebook lookalike audiences. That’s another benefit of having channel partnerships early on, the first customer indicated what the next 10,000 customers would look like. If you’re not familiar with Facebook lookalike audience, that basically means once you figure out the first 1,000 kinds of people based on their information and whatnot, of course, making sure that privacy and security are being kept in mind, Facebook will then help you find the next million of those individuals using paid advertising. That helped us achieve nearly a 2x to 4x return on assets. Most startups when they launch, they don’t see anything near that, but because of our channel partnerships, because we knew what kinds of people to go after, we’ve been able to generate revenue that most startups will only dream of generating in the first two years, we’ve been able to do in the first six months of being able to launch.

I also want to share my thoughts about working with friends. So having learned something from hearing the feedback over and over again that solopreneurs and solo-founders don’t get investment, well, I did raise capital when I was building my last venture-backed company. But one of the things that other venture capitalists and seasoned entrepreneurs told me over and over again is that we prefer co-founders, we prefer more than one founder. I totally get it, it’s a risk mitigation effort. If you’re putting in like 50 grand or 100 grand, for most people, that’s a lot of money. But when it comes to talking to a fund or an angel investor that’s accredited, that’s not a lot of money.

I was under the pressure that I need to find a co-founder. So I looked around I said, who has a similar knack for design, a similar knack for attention to detail, and could compliment me with the skills? Because I’m more of a creative and I’m also a front-end developer, but I needed help on the finance side and the legal side. Well, it just turned out that one of my friends from college had a friend who he grew up with, that was majoring in accounting, and his dad was a lawyer as well. So it was like, that’s great. For a couple of years, I knew him, and he had very much a sense of design that we were looking for. So if anyone has ever used HelloWoofy or is looking to sign up, you’ll notice that everything in the product is pixel perfect, design-oriented, color-driven, and very minimalistic. I’m inspired by Danish furniture when it comes to minimalist design. He was very similar as well. So I was like, this is perfect, let’s make it work.

Unfortunately, he doesn’t have the experience that I needed. I knew that going in, but I was like, let’s give it a chance, let’s try to work this out. The first few months were great, and even the year was great. But when it came to getting the introductions from our investors, one of our investors specifically, it became very apparent that the new shiny thing that would be one of the engineers I was introduced, was not a good fit. So he started making decisions that were under the influence of that individual, and were not helpful to the company, were not helpful to the product, were not helpful to anything. So I came to know about other things, which doesn’t really matter. We basically collectively made a decision between the investors and the advisors and myself that we have to let go of both, the engineer that was introduced after by the same investor, as well as my co-founder. Because they were just not up to the par, they were faking their way into the company, and they didn’t actually have the expertise needed from an engineering standpoint to build the right product to ship with. In my co-founder’s case, it was just a culture misfit, and unfortunately, I had to let him go.

We dealt with that from a legal standpoint settled, all good, taken care of now, and I wish them the very best, of course, going forward. But we’ve decided to turn the company around, I still owe a lot to my investors for believing in me, specifically, since I brought most of the capitals to the table. And we were not going to let that go. So that’s why I put everything on the line, and within the last year and a half or so, we turned the company around. That’s what I was discussing earlier, we are on our way up. We’ve grown 16,000%, so I think we’re doing something right in six months. They say a fire for something really big and you might get a small percentage of it, but our goal from the get-go has been very ambitious to take on the world of social media marketing first, now blogging, now direct to consumer marketing with Amazon Alexa Scheduler. Our ambitions are only going to expand, so who knows what’s next!

So you can go to, take a look at the product, even email me. I want to know about your small business story, if you’re a virtual assistant or you’re a mom and pop store, and you need help with digital marketing, any facet of it, social media marketing, reach out to me because that’s the most we can do, is giving back to the small business community that is actually helping us. In fact, one of the things we didn’t talk about is our equity crowdfunding element, we’ve been raising capital from our customers who now own a piece of the company that is growing along with them. It’s a very new way of running a company and raising capital. You can go to to learn more about how you can invest as low as $100, own a piece of the company, and use the product at the same time. So email me, let me know how I can help you. If you use the product, give me feedback, tell me what I need to build with my team to address your needs as a small business owner. We love talking to customers in both our Facebook group, Content Masters by Hello Woofy, as well as email or social channels as well.