Blog

  • Unrealistic Goals Can Hurt Startup Morale

    In my early years of entrepreneurship, I was intensely focused on setting big, hairy, audacious goals and shooting for the moon. My approach involved dreaming big, working hard, and rallying the team around the exciting opportunities ahead. Over time, I’ve become more tempered, setting a big vision but adopting a more measured approach to the incremental steps needed to achieve it.

    It’s straightforward to declare, “We’re going to sign 1,000 customers in three years.” However, it’s a different proposition to articulate a vision of winning the market and becoming the de facto standard. For example, planning to sign 50 customers in the first year, 100 in the next, then 200, 500, and finally 1,000 allows you to maintain a big vision—like a computer in every home or organizing the world’s information—while adopting a more measured approach to achieving it.

    Over the last 24 months, the software industry has been in a recession. This period has necessitated numerous reforecasts in our businesses. A reforecast involves reassessing your plan partway through the year upon realizing the original goals are unattainable—not just challenging, but so far from achievable that a new plan for the remainder of the year is required, aiming for better alignment, efforts, and outcomes.

    During this software recession, the need to conduct several reforecasts each year has underscored to me that setting unrealistic goals can actually harm startup morale. Goals should be challenging yet achievable. With good faith, effort, and smart, diligent work, they should be within reach. However, if goals are unrealistic and the team’s efforts fall significantly short, this can have detrimental effects.

    As an entrepreneur, it’s crucial to find that balance for your organization—setting ambitious goals without making them so lofty that they become unrealistic and harm morale. It’s a delicate balance with no straightforward solution. Entrepreneurs would do well to find their own approach to this and be intentional about how they lead their organizations in respect to goal setting.

  • Simple Financial Distillation as a Mental Model

    Yesterday, I met with an entrepreneur, and we discussed a variety of ideas related to building community. Late in the conversation, he shared one of his favorite mental models and asked for one I liked. After thinking for a second, I knew my go-to: simply distilling the financial model or business down to its most basic format. The idea behind this exercise is that if the financial model doesn’t work at the most basic level, it’s unlikely to work at a more complex level. Conversely, if you can’t break it down into a simple form, understanding it at a complex level becomes challenging. If it’s so complicated that you can’t understand it or help others understand it, the chance of success significantly decreases.

    Let’s look at a couple of examples. In the first example, with software as a service, it’s easy to describe what the product does, whom it serves, and how it will work in the real world. Even with all that, if it’s not clear that our business model is to sign up 1,000 customers, who will pay us $10,000/year, and we plan to sign up this many more customers over the years, and we believe that with the gross margins and everything else, it will be a viable, if not great, business, then all the other pieces don’t matter. Of course, businesses are much more complex than that, but at a simple level, what is the financial model?

    Look at a second example. If you talk about something like co-working space, it’s a similar pitch. How do you distill the business model as simply as possible? We’re going to have 200 desks and we’ll charge $350/month per desk surrounded by incredible community and services. This will provide the scale and revenue to offer an amazing experience to our members. 

    When thinking about different businesses and exploring entrepreneurial opportunities, my go-to is a simple distillation of the financial model in a way that can be described quickly and easily out loud. Start simple before adding complexity.

  • In the Playbook of the Future Acquirer

    Last week, I caught up with an entrepreneur, discussing how things were going with his startup. We delved into the usual topics, sharing what we’ve learned over the years. A question arose: “What should you do to prepare for selling your business in the next couple of years?” After pondering, I shared a pivotal course of events before a highly successful exit.

    The eventual acquirer, a holding company with a diverse tech portfolio, had one of its companies become our customer. Their positive experience led to a referral to another portfolio company. Gradually, several more became customers. Recognizing the value, the holding company decided to integrate our solution into their playbook for all subsidiaries. As we continued to excel with more portfolio companies, we became the obvious choice for acquisition. We were a) a preferred vendor, b) already integrated into multiple subsidiaries, and c) standardized in their operations. This made the acquisition a seamless, win-win situation: they knew exactly what they were getting and how to leverage it for future growth.

    While there’s no surefire strategy, having your software adopted as a standard by a business or strategic partner can create a strong acquisition opportunity. My advice for entrepreneurs is to look for ways to deeply embed their products or solutions in a manner that’s more than a standard customer/vendor relationship. This not only strengthens your market presence but also opens doors to a potential acquisition in the future.

  • Question the Repeated Advice from Experts

    Last week, I was catching up with an entrepreneur, and he shared with me that he kept receiving the same advice over and over again. However, after digging deeper and analyzing it from a first-principles perspective, it just didn’t make sense. We talked more and tried to delve deeper into it, and it became clear that there was a difference of opinion between what the entrepreneur believed and the commonly accepted advice he was receiving.

    This reminded me of the early days of Pardot when our business was two years old. Things were growing fast; we had over $1 million in recurring revenue, and everyone kept telling us to go raise venture capital. Not knowing any better, we talked to investors in Atlanta, Washington D.C., Boston, and all over California in an effort to raise money. We had dozens of meetings, were on numerous flights around the country, and in the end, we received two offers. When we analyzed the numbers and plugged them into some spreadsheets, we realized it didn’t make sense to raise money. We were growing fast, had great gross margins, and especially with the valuations at the time, it just didn’t add up. We were better off growing organically at the rates we were and controlling our own destiny.

    Once an entrepreneur raises money, it’s almost impossible to unwind it. But for entrepreneurs who haven’t raised money or have only raised friends-and-family money, the ability to control one’s own destiny is incredibly valuable. Ultimately, we chose not to raise money for Pardot. We kept growing the business and had a great exit three years later.

    My advice to entrepreneurs, when they receive repeated advice on more material topics, is to question it. Peel back the layers, understand who is saying it and why they’re saying it. Do they have an agenda? What’s their personal experience been? Work hard to see if that aligns with the goals and dreams of your own company. While most of the time, advice will likely resonate and be applicable, there’s a chance that serious recommendations, when critically examined, may not be good advice for your own business. Always question the repeated advice from experts.

  • The First Serious Acquisition Conversation

    Late in 2012, we sold Pardot to ExactTarget and it was subsequently acquired by Salesforce.com. Only in January, the year before, we were actually in discussions to sell the business to HubSpot. At the time, HubSpot was focused on content marketing, search engine optimization, blogging, and analytics. They realized that marketing automation and using the web for email marketing, lead generation, and lead nurturing were the next big opportunities.

    So, they decided to evaluate potential acquisitions in the market. For us at Pardot, we had built a strong micro brand. We had a number of customers who loved us, were growing rapidly, and had the start of a platform. In late 2010, we received an inbound email from HubSpot asking if we were available to discuss partnerships. We got excited and thought about partnering with the content marketing giant that we admired.

    After some back-and-forth it was clear that a “partnership” wasn’t the intention, so we scheduled an on-site meeting for Adam and me to fly up to Boston in January 2011. Of course, we prepared extensively for the meeting thinking through potential questions, built a new slide deck, and headed north. We arrived in Boston with plans for a full day of meetings followed by dinner and a return flight the next day.

    During our visit, we had the opportunity to meet with Brian and Dharmesh, the founders of HubSpot, their executive team, and David Skok, a prominent VC on their board. We spent hours discussing the business, the market opportunity, and shared all our metrics. We talked about the potential to work together and had an incredible working session with their team.

    After our meetings, during a small founders-only dinner, we had the chance to talk with Brian and Dharmesh. We discussed why they started HubSpot, their goals, what had worked well, what hadn’t, and their startup philosophies. It was a unique experience, as there are only a handful of times in a career where you get to sit down with like-minded entrepreneurs who so closely share your vision.

    By the end of dinner, Brian and Dharmesh floated an acquisition offer. The offer was roughly $10 million in cash and $20 million in HubSpot stock. At that time, HubSpot had just raised financing from Sequoia Capital, valuing the company around $300 million. Our annual recurring revenue at Pardot was about $5 million and growing 100% year over year.

    Adam and I considered the offer carefully. We wanted more cash upfront, given the uncertainty of illiquid stock in another private company. We went back and forth, suggesting an increase in the cash component. If not, we were willing to sit tight and continue growing our business.

    Ultimately, HubSpot chose to go its own way and continued its incredible growth. Today, HubSpot is a publicly traded company valued at close to $30 billion. Meanwhile, we at Pardot stayed the course and kept building our company.

    About 18 months later, we decided to sell the business to ExactTarget, which was quickly acquired by Salesforce.com. Thanks to Salesforce.com’s efforts, Pardot became one of the most widely used B2B marketing applications on the Internet.

    Looking back, it’s always fun to reminisce about what could have been. It’s enjoyable to think about the experiences along the journey. The opportunity to spend time with Brian, Dharmesh, and their team, and consider what it would have been like to merge our companies, remains a fond memory.

    As an entrepreneur, it’s essential not to get too caught up in the potential exit. The focus should be on enjoying the journey and continuing to build a great business. In 2011, we had one of our first serious opportunities to consider selling, but we chose to stay the course, and were better off for it.

  • Pleased but not Satisfied

    Last month, I was talking to the leader of a well-known organization about his approach to achieving excellence. We shared some of our own personal best practices and learnings over the years. He shared one that really resonated with me: the idea is to be pleased but not satisfied.

    This involves pushing the team hard and having a strong opinion on how things should operate. The idea is that there’s a balance between encouraging the team and individuals to do their best while also finding opportunities for them to do even better. Sometimes it’s easy to take what you get and move on, and sometimes, you know that more is possible.

    Late in the Pardot years, we were making a push for customer referrals. Our sales team would ask for referrals after a new customer had a successful launch. Customer success would occasionally ask for a referral after an excellent check-in call. It was okay but not great. I pushed the team. Surely, there were other options. Then, after pushing more, the answer emerged: an in-app Net Promoter Score questionnaire once a quarter, and for users that were promoters, an automated prompt for a referral in exchange for a $100 Amazon.com gift card. Bingo. The referrals flowed in. Pleased initially with the referral push, I was not satisfied until we achieved better results.

    As a leader and manager, you have to find that balance. Do you push more, or do you take the progress and be done with it? My favorite saying, after reflecting on this and thinking more about his perspective, is exactly how he described it: you want to be pleased but not satisfied. You want to share with the team or individual that you like the progress and the direction, but you’re not satisfied. There’s always something better, a next level, a new realm of possibility. So, the next time you’re working with a team and the result comes back, but you know even more is possible, tell them you’re pleased, but not satisfied. Stay hungry for more.

  • Relief Valve During Stressful Periods

    Last week, I was talking to an entrepreneur, and we got to the topic of ways to relieve stress during especially difficult periods. He shared some of his past experiences, and I shared one of mine that I remember vividly. 

    Back in mid 2012, we were going through the process of selling our company. As part of that experience, there were a couple of months of negotiations, which had a little bit of stress. Then, as we got deeper into the negotiations, the stress ramped up. In the final two weeks, the stress got unbearably high for me personally. Then we signed the letter of intent to sell the business, and we had this 45-day due diligence period, driving stress up even further. 

    If everything went according to plan, our company would have a new owner, and my life personally would change dramatically. Not knowing how to handle this anxiety, stress, and looming deadline, I looked around and tried to find something to occupy my mind, especially when I was caught up on everything related to the acquisition and the day-to-day running of the business. For me, I arrived at something pretty simple: staring out the window while working on my laptop. I would look at the backyard and see a bunch of grass with weeds in it. So, as soon as I finished what I needed to do at the office, I would go home and hop on a little gardening cart and pull weeds to clear my mind. One by one, little weeds, medium-size weeds, I’d fill up the garden cart, take it to the back bushes, dump it, and then start over. No phone, no laptop, no podcasts, no distractions, just me, a garden cart, and a backyard of turf. 

    So for that 45-day period, and even a bit before we got to the due diligence, my go-to activity when I cleared my most immediate tasks at home was to pull weeds. This experience and this process of having a stress release valve made a huge difference. We got through the transaction, sold the business, and announced the sale to the world. It was off to the next chapter in my professional career. 

    My recommendation for entrepreneurs is to find a relief valve during stressful periods. For some, it’s going on a jog; others, it’s playing video games. Some love to cook or read fiction. In the end, it’s important to have something that works for you so that when the stressful times occur, and they always will, you have a relief valve ready to go.

  • Expertise is Plentiful Outside Venture Firms

    A decade ago, I was helping an entrepreneur with a fast-growing, successful business. At the time, he felt that he had to raise venture capital. Initially, I thought it was the typical story of needing more money, the opportunity to capture market share, and the desire to grow faster. Only after digging in some more did I realize that his main reason for wanting to raise venture capital was a combination of having someone experienced to ride alongside him and the expertise offered by this particular venture firm. This expertise is often positioned with terms like “centers of excellence,” “operating partner,” or “consulting teams,” which are basically in-house specialty functions within venture firms to support entrepreneurs.

    This approach was originally popularized in the Hollywood world and then adapted to the venture world, made well-known by the venture firm Andreessen Horowitz, also known as A16Z. For this particular entrepreneur and the venture firm he was talking to, it wasn’t A16Z, but it was another firm with a great reputation and a strong consulting team as part of their offering.

    After spending time with the entrepreneur to understand where he really wanted help—with respect to pricing, packaging, recruiting, strategic planning, and product management—it became clear that what he really needed was a series of boutique consultants, experts in their craft, that he could call and build a relationship with. He could develop a retainer fee structure if needed but really have direct access to these specialists. He did not need to raise venture capital to do so.

    After six months of playing the fundraising game and going back and forth as to whether or not he should take the money, he ultimately decided not to. He continued to grow the business organically and build out a network of experts to hire directly without having to take on venture capital.

    My recommendation for entrepreneurs looking for help and expertise in their business is not to feel like they have to raise venture capital to find people who can help. The great thing about the startup community and the size and scale of the startup industry is that we now have experts across the board. Founders would do well to build out their own team of experts.

  • Strong Vision to Repel Distractions

    Just this past week, an important topic has come up twice: the idea of having an incredibly strong vision to repel distractions. On Thursday, I was talking to an entrepreneur, asking about his favorite piece of advice for new entrepreneurs and initiatives. He mentioned that with a clean slate, energy, ambition, and excitement, it’s easy to get inundated with other people’s ideas, dreams, and pet projects. One of the most important things an entrepreneur can do is to have a really clear, strong vision for how they want the world to look and use that as a lens for all incoming requests. Think about it: with opportunities to do anything and everything, the chance of chasing the shiny object or getting distracted is incredibly high.

    Personally, I remember in one of our earliest companies, we were desperate to keep the lights on and had some software sales coming in. A customer made a request for a feature that didn’t fit our vision of the world, but we were so focused on generating revenue that we said yes. We built this feature, very specific to this one customer, and rolled it out. We got a little bit of money from it, but no other customers used it. The customer that had to have it churned, and now we had a bunch of code cruft and technical debt that had piled up over the years, which we had to unwind. The process of unwinding and refactoring was a much greater headache than the cash received from the one customer. Now, the flipside of that is maybe we had to do that work to keep the lights on, and maybe we should’ve had a different approach to how we implemented it. But knowing what I know now, if we were confident that we were going to keep the lights on outside of that customer and without building that new module, I am sure that we would’ve been better off staying the course on our vision and not doing a one-off feature for one customer.

    Entrepreneurs, by their very nature, are eager to build, sell, and make progress. So when you add it all together, it creates an environment where distractions, requests, and feedback are plentiful. One of the most important things an entrepreneur can do is have a strong vision to repel distractions.

  • Mochary Method Curriculum for Founders

    Every once in a while, I come across a document that blows me away with its contents. In today’s example, startup CEO coach Matt Mochary has built one such information source, and every founder needs to know about it: Mochary Method Curriculum

    In the journey of the founders’ experience, it’s important to have context and relevant information based on what’s happening at that moment in time. For example, if there’s an article about raising a $100 million late-stage round, that article isn’t applicable to a seed-stage entrepreneur trying to find product-market fit. The great thing about the Mochary Method Curriculum is that it has valuable, mostly general-purpose information, from hiring to firing, to board meetings, to product development, to the emotional side of running a business, to the personal health and wellness side of being an entrepreneur. 

    Based on the contents of the articles contained in this curriculum, it’s clear that Matt has had the opportunity to work with a number of exceptional entrepreneurs over an extended period of time. The wealth of knowledge in these documents is tremendous. 

    My recommendation is for every entrepreneur to visit the Mochary Method Curriculum, bookmark it, and revisit it on a weekly or monthly basis as new challenges and opportunities arise in their business. It truly is one of the most remarkable curriculums for entrepreneurs.