MBA, Accelerator Or Just Go For It?

You’re in your mid-to-late 20’s and your thinking about being a first time entrepreneur. Maybe you already have an idea for a solution to a problem that needs solving or perhaps you just know in your bones that the entrepreneurial journey is your destiny. You’re probably in your first or second job after undergrad and feeling like now’s the time to figure out how to make the most of this “prime time” in your life – this is the tail end of your defining decade. Perhaps this is the right time, before you have family or other life commitments; or maybe because you feel if you wait too long, you’ll never do it. 

Regardless of where you are in life, if you’re feeling like you are at a cross roads in the early part of your entrepreneurial journey, you probably fit into one of these categories:

Screen Shot 2019-07-23 at 2.44.18 PMI see aspiring entrepreneurs approach these categories in a few ways: Learning as they start their companies, enrolling in an MBA or certificate program and/or applying to a startup accelerator. Some also choose to join an early stage company while they noodle their idea(s) so they can see how others do it and learn from their successes and failures before they strike out on their own. There are pros and cons to each approach and each is a highly personal decision based on your risk threshold, what you’re building, and who you are as a human being. There is no “right” way to do it, but here are a few ways to think about each approach, noting that sometimes doing more than one can be the best formula. 

On the Job (OTJ)

I am a big proponent of experiential learning. Touch a hot flame, you know not to do that again. Take an active listening role face to face with a customer and you’ll learn more about their needs and how you can solve them vs. running a survey or doing passive research on-line. However, some might argue that OTJ learning is a “two steps forward, one step back” approach as you’ll make a lot of mistakes along the way. Some mistakes will be recoverable, but some may be life threatening to your business and almost none of these mistakes can be predicted. Many of the most successful startups got that way because of luck and timing or because they had made/raised enough money to dig themselves out of a hole or two until they got it right.

OTJ_Poll

Questions to ask yourself if you are thinking about this approach:

  • What is your pain tolerance in terms of how far you can stretch your money, lifestyle and idea? Your about to get on a roller-coaster. Do you think you can handle it? Are you ready to hear “no” a lot and live off of ramen noodles and pizza indefinitely?
  • Do you have a strong network of mentors, coaches, advisors, investors and friends to get advice (and potential capital) from? Do you know how to get that advice/money and will you take it or not?
  • How easily do you make decisions? Will the noise of endless advice, competition, differing opinions from employees/co-founders/investors thwart your progress?
  • Are you a good salesperson? Can you recruit talent, fundraise and acquire customers?
  • Do you understand the product development process for your idea? Have you fully explored the problem to be solved, who you’re solving it for and the potential solutions? Do you think you have an MVP that will get you off the ground as you work towards product market fit? How confident are you that there’s an addressable market worthy of you/your co-founder and/or investors taking a risk of time and money on this idea?
  • Are you as in love with the problem you want to solve and passionate about the possible solution as you are in love with being a leader/CEO? Where is your ego in this process? Starting a company is one of the most humbling experiences you’ll ever have – it’ll touch your insides in ways you never thought it could. Are you ready for that?

If a few of the above points give you pause, either figure out how to resolve them before forging ahead, or consider some of the other options below.

Applying To An Accelerator

I’m a big fan of well structured accelerators with strong reputations for developing entrepreneurs and their products (e.g., Y-Combinator (YC) or TechStars). The programming is usually very solid and the results are almost always positive – companies are typically much further along with their business plans and messaging by their usual culminating event, “Demo Day”. Fundraising is also a big part of an accelerator program and the better ones have a pretty strong network of investors eager to fund each cohort. That said, in my recent Twitter poll, 50% of the respondents said that the network was the top benefit. I’ve seen this firsthand from my years of experience as a mentor with TechStars. Whether it’s needing help with introductions, getting advice on business strategy, building products or even just a shoulder to cry on, these networks have proven to be invaluable for entrepreneurs who’ve gotten into a quality program.

accelerators

There are many accelerators out there. In addition big brand names like YC or TechStars, there are a myriad of others that range from niche areas (biotech, robotics, healthcare, fintech…) to city-specific, to those that cater to underserved populations, etc. The list is endless! Here’s how to think about applying to accelerators:

  • Figure out which accelerators are a fit for your idea/company and what you want to get out of their program. It’s no different than applying to college – everything from where you want to live to who you’ll hang out with 24×7 counts in the decision process.
  • Make sure your idea/company is far along enough to apply. I often see founders trying to apply way too early and while it can be a good experience just to go through the process, it’s a big time waster for you, your company and for the accelerator who is evaluating your application if you are not at the right stage.
  • Talk to alumni from programs you’re considering. Find out about their application process and any lessons learned (things they think they nailed, what was the program worth it to them, tips on how to get the most out of the program, etc.)
  • Understand program expectations while you’re running your business. Many founders who get into the more intense programs don’t appreciate how hard it is to keep the momentum of their business while going through the program. It’s like having two full time jobs!
  • If you are definitely applying to a program, line up your references in advance and try to get warm intros to the Managing Directors (MD) of the program. Warm intros are worth a lot in all parts of business, accelerators included. Also, you may find that a warm intro can serve you well if your timing was out of sync with the accelerator’s application process. Sometimes. a company drops out of a program last minute, just before the start date, and a warm connection with the MD could be the fast track to fill that open spot (several companies I’ve worked with have been accepted into programs because of this situation).
  • Apply to more than one and know that some may push you to another location of theirs or class depending on where you are in the process, stage of your company, other cohort needs, etc.
  • If you don’t get into a program, either decide if the time to apply was worth it (maybe it forced you to learn more about you, tune the story of your business or products?) and try again, or move on and keep on trying to accelerate your business on your own.

Getting Your MBA

There are countless reasons one should or should not get an MBA, all of which I will not cover here, but if you are thinking about how to learn about entrepreneurship or further your business, it can be a great way to go. Of course, in most cases it is very expensive and yes, it’s ~2 years “checked out” of the real world, but in the right type of program, it can be a great solution.

DISCLAIMER: I am on the faculty at Harvard Business School, but I try to be unbiased here and cover more general aspects of MBA programs with an entrepreneurial focus. Also, full disclosure: I enrolled in a dual MS/MBA program early in my career and in the end I only completed the MS as I found that particular program adequately met my career needs. I was also self-funded, and in debt from undergraduate school; despite some scholarship money, the added debt was untenable. Most B-schools now have great financial aid and fellowship programs (50% of our HBS students get fellowships), but MBAs are still not for everyone!

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Considerations for whether to apply to an MBA program with an entrepreneurial focus:

  • Cost – can you afford both your time and money?
  • Do you have an idea/company already in process that you want to move forward? How will the particular program help you do that? Are there specific courses for your stage of business, industry or problem you’re trying to solve? Are there faculty, peer mentors or other on-campus experts available to students starting businesses? Is there time during the program to actually work on you company (e.g., experiential courses where you build your business for credit, summer programming, etc.)
  • Do you want to be somewhere where you can find an idea and/or a co-founder? Are the programs you’re looking at known for incubating new ideas and/or fostering co-founder relationships?
  • Are you unsure if you want to be a founder, but would at least like to become a joiner to learn more about startups? Do the programs you’re evaluating offer opportunities for joiners to meet founders building their companies while in school? Do they offer courses that educate the joiners as much as the founders?
  • Beyond the curriculum, what e-ship programming is available in a given program? Do they run accelerator programs or have space for young companies to connect and incubate their ideas?
  • Is startup funding available such as contests, access to venture funds, loan forgiveness for startups coming out of the program, etc.?
  • What access do students have to the school’s network such as alumni, the local startup community, investors, other universities in the area etc.? How do they add value to the entrepreneurial experience of admitted students? Will this network fill in gaps in your current network?
  • If you’re considering the venture side of entrepreneurship, do the programs you’re looking at have an investment-oriented curriculum and/or opportunities for aspiring investors to experiment with investing and learn to work with founders while in school?
  • Finally, what is the entrepreneurship track record of a particular program? How many startups were founded by their alumni (either while in school or within five years of completing their MBAs)? What is their alumni companies’ funding track record? In what other ways are their alumni founders successful (revenue, social impact, focus on diversity & inclusion, strong and ethical business ethos, etc.)

In the world of entrepreneurship, there are so many variables to consider when making just about any type of decision – from what product to build, who to hire, how to sell and how to finance your business. The list is endless and extremely tied to the type of business you are building, your customers and who you are as a leader. Similarly, which route you take to develop your entrepreneurial skills is highly personal. The route one entrepreneur took that worked out well for them does not ensure the same will hold true for you. Consider all of the above and decide which one or combination of all options makes the most sense for you.

Have you done one or several of the above to help kick-start your entrepreneurial journey? Please share your experience and lessons learned in the comments!

Reflecting On The Intersectionality Of Today’s Pressing Issues

I was so moved at tonight’s event at The Wing in SoHo that I had to write. In the spirit of the anniversary of Stonewall, we had an extremely thoughtful panel of rockstars:

  • Cecilia Gentili – Transgender activist, actor and someone who speaks with deep empathy from countless experiences throughout her lifetime.
  • E.M. Eisen-Markowitz  – Restorative (and Transformative) Justice Coordinator and public school teacher.
  • Wazina Zondon – Founder of Coming Out Muslim and sexuality educator.
  • Alex Berg – Panel moderator, and journalist covering national news, women’s issues, and LGBTQ+ culture. 

My twenty year-old daughter, who has been openly queer from a young age, joined me tonight as my guest. As we walked home, we processed key points from the discussion. A few worth noting:

  • We are privileged white women and we and our family, friends, colleagues, etc. are not doing enough to support real change in this country for the LGBTQ+ community. Putting strong light on the issue and companies changing logos and decorating storefronts to rainbows a few weeks a year is not enough. It’s a conversation and action that needs to happen every single day.
  • The majority of people who are speaking up and fighting for change are putting themselves at risk ahead of those of us who can afford to take real risk. Reflecting on Stonewall, Cecilia highlighted that it was the white privileged professionals who ran from the scene and the less privileged crowd that put their lives at stake to fight back – people who could not afford bail money if arrested or perhaps survive if they were to be imprisoned. 
  • Wazina gave us pause around how we’ve been talking about reproductive rights. This is an intersectional issue, not just a white feminist issue or about who can tell whom what they can do with their own bodies, it’s also a parenting issue: who is ready to be a parent and what that means (emotionally, physically and economically). I applaud her for the work she’s doing with young people around this and other important health, identity and sexuality issues.
  • EM spoke of transformative justice inside schools to change the narrative and behavior vs. the crazy spend in NYC schools to police the problem (over $700M/year!). This is an important issue well beyond our city schools. We need to transform society.
  • On D&I and hiring, we heard stories of companies seeking to be inclusive that are not removing barriers to allow a diverse pool of candidates to apply simply by creating exhaustive list of requirements in the JD (see more of my thoughts on this here). Provide training, mentorship and tuition reimbursement for applicants who have the aptitude and lack the experience. Make it happen vs. complaining “we can’t find the ‘right’ candidates”.
  • Finally, know your political candidates positions and vote for those who understand these issues and are motivated to take action. Now more than ever, we need the right people in office.

I’m definitely going to think deeply about how I can make a bigger impact on these points and take action; with my voice, my dollars and my body if I have to. I suggest everyone else do the same – educate yourselves, open your minds and take action. 

Thank you to the events team at The Wing for organizing this evening! My only constructive feedback (‘cuz you know I have it!) is that there were not nearly enough of your members there or PR around it. We can do better.

Beyond Their Funds, How Can Your Investors Be Helpful?

An entrepreneur recently said to me “When it gets really hard, I feel like I’m doing it wrong.” She went on to say that sometimes she’s not sure how her investors could be helpful — even if it’s just validating what’s hard vs. advising on how to work through certain challenges. I’ve heard other entrepreneurs say they’d like to get help from their investors but worry that purely by asking for help it will signal a weakness. Conversely, I’ve heard investors say they wish the leaders of their portfolio companies would be more transparent about challenges they are facing and ask for help. As one investor said to me recently, “They already sold me on the business and have our money. It’s now our firm’s job to help them succeed.”

In an informal Twitter poll I recently conducted, 56% of entrepreneurs who responded said their most common ask of their investors is for hiring help. Second to that (31%) are asks for introductions to potential partners or customers and a small percentage (13%) tap their investors for financial management advice.

I also polled my investor friends on what questions they like to get from their portfolio companies. What they shared made it clear to me that they can and want to be helpful well beyond their funds!

“Good entrepreneurs are learning machines so they’re always asking for advice and guidance from multiple sources of expertise, including their investors. In fact, the best founders are outstanding at squeezing every bit of insight, advice and contacts from their network of investors and advisers.“ Jeff Bussgang, Flybridge Capital

Do you know how to get the most from your investors? Below, I have outlined what I consider to be basic asks (table stakes) as well as suggestions for deeper asks.

What To Ask For

Hiring

Table Stakes:

  • Referrals and warm introductions
  • Posting job links on their websites
  • Invitations to recruiting events

Beyond the Basics:

  • Seek examples of job descriptions (JDs) and/or critiques of those you’ve written. Most investors were operators once and have a good sense of how to write a good JD; they may also have a recruiting arm at their firm who can counsel you on specific searches. [See point on compensation in Financials, below]
  • New to hiring? Practice interviewing candidates with investors or their associates before bringing actual candidates in for the real interview.
  • Resume screening can be an easy ask and a quick job for someone who’s seen 100’s if not 1000’s of resumes. Experienced eyes can point out immediate red flags and give you specific areas you may want to probe for a particular candidate.
  • Invite an investor to help diversify an otherwise homogeneous interview team. This can be a game changer for a candidate who may otherwise feel like they are a token hire. Knowing the extended team around the business is diverse, can allay these concerns.
  • Ask your investors to help sell the business to prospective candidates. This can be especially critical if you’re trying to hire a senior team member or a start-up first-timer.

    “This is something we continue to do, even with mid-level hires in mid-stage companies when the founder feels like a highly desirable candidate could use an extra push. It’s not a huge burden on our side, but can have a very strong positive impression on the candidate who probably feels like getting board/investor visibility is a strong positive in their career development. “ Rob Go, NextView Ventures

  • Investors can also be helpful offering insights on how your company is perceived as a workplace from their own perspective or from feedback they’ve garnered in the market. (people talk…)
  • Finally, but very carefully, investors may be able to help you get backdoor references on potential hires. I wrote more about this particular topic here. Backdoor references can be helpful, but only if done right!

Marketing, Sales & Partnerships

Table Stakes:

  • Introductions to potential customers and/or partners
  • Putting your company logo on their website; putting their firm’s logo/board member on your website
  • Invitations to marketing & sales events
  • Tapping their social media presence for sharing news and events

Beyond the Basics:

  • Investors look at markets all day, every day, and have an objective perspective on not just current market forces, but patterns over time and how markets move and customers buy. They may not know your specific market details or the intimate buying patterns of your target customer, but as Bob Mason of Project11 says “We often ask the right questions informed by our opportunity to step out of the day to day urgency of running the business. We have enough knowledge to understand the big market forces, see patterns from other businesses and can help drive an engaged dialogue. For the engineering-centric founders, you can think about this as ‘debugging’ an issue. When coding, you might bang your head for hours trying to find the root cause of a hard bug. But you bring over a colleague and talk through the situation and often a solution will appear. They didn’t tell you the answer, but the process of conversation brought insight to your mind.”
  • Whether you are building an enterprise product and need access to a buyer inside a potential large customer or trying to develop partnerships for your business (B2B or B2C), investors can provide invaluable insights on what drives particular companies, who the “real” decision makers are and how their buy/partnership process works. They can reach out to execs at companies and get an early feel as to how important such a potential deal or relationship could be.
  • Investors are generally good at analyzing marketing or sales funnels. If they are former marketers or sales people, they should be able to help you understand the “magic moment”, points of stickiness, drop off, etc.. They also won’t have the biases you likely bring to the table and can look at the numbers objectively.
  • Investors can be helpful with developing your company and product story as well as speak with folks in the industry to see how the story resonates.
  • Beyond offering advice on digital marketing and leveraging social media, your investors may also be helpful with brand awareness and offer PR opportunities. Perhaps they are sponsoring an event where you or a key member of your team can be a speaker? If one of your investors is a blogger, ask for a mention in their next blog post about a topic you’ve been discussing, or perhaps even a guest blog spot. Be creative about how your investors can help shine a light on your brand, product and team!

Product

Table Stakes:

  • If they can use your product as a firm or as individuals, they better be using it! Whether it’s for testing the MVP or to dogfood the brand, no excuses. There’s nothing more compelling than an investor who offers you a cup of coffee made with one of their portfolio company’s new beans or the investor who has a “powered by” one of their companies on their website. Have you asked your investors to use your product?
  • When asked (or not), investors never lack for advice on how your product can improve. Just remember, you are in it every day, they are not. So, always weigh that advice against what your team is discovering with your customers and progress accordingly.

Beyond the Basics:

  • If your investor is a former operator, especially at an early stage company, odds are they have built/tested many an MVP. Engage them in the MVP discussion. Review product priorities and test plans. Again, their objectivity and experience could give you a fresh perspective. This will also help them understand the tradeoff decisions you are making and can be very informative when it comes to strategic thinking about the company’s product roadmap and long term direction.
  • Speaking of roadmaps, if you’ve got a former head of product or VPE on your investor team, invite them to a planning session. Same reasons as above — fresh perspective and added insight when it comes to bigger picture discussions.
  • Security and compliance is an area often overlooked and where investors can probably draw on their own or other resources to ensure your company doesn’t get tripped up on a sale or regulatory issue because an “I” was not dotted or “T” crossed. They may have access to pen testers or be familiar with compliance requirements for things like PIAHIPPA or SOX through other portfolio companies’ experiences; even if it’s just asking when to worry about it vs. holding off on investing in this work.
  • Also helpful is tapping investors’ technical EiRs and/or network. When I was CTO at DigitalOcean, it was amazing to have someone like Martin Casado at a16z, our lead investor, to bounce ideas off of and even help us with some tricky architecture decisions. Similarly, my friend Jocelyn Goldfein of Zetta Venture Partners said she’s often tapped by her portfolio companies to help with developing data strategies and answer questions about data rights. Know who the experts are in these firms and they’ll probably love the opportunity to get into the details with you since it’s no longer their day job.

People

Table Stakes:

  • If they are involved with financial planning, investors should be helpful with basic headcount and organizational growth plans (what roles to fill, how many and when)
  • Investors are generally not shy about telling you (sometimes unsolicited) if they think a key employee they are interacting with is great, needs coaching or may not be successful in your organization. Just remember, if you have a board, other than the CEO, they don’t make hiring or firing decisions. That’s your job.

Beyond the Basics:

  • Whether they were former operators, or have just seen a large number of companies operate, investors can give helpful insight around people and culture. You can ask how to work through team challenges, enhance your company culture or even how to make remote teams work. If they’re not the experts in these areas, they likely have companies in their portfolios who are doing creative things or who maybe learned from mistakes and are willing to share tips and tricks to avoid pitfalls as you scale.
  • While it may make you feel vulnerable, asking your investors for guidance around your own personal development demonstrates your willingness to grow — especially if you are a first-time CEO, or other member of the C-Suite. I’ve seen investors coach leaders on everything from how to lead their teams and handle challenging employees to how to run a great board meeting. I’ve also seen investors support and sometimes even pay for executive coaches and training programs for high-potential leaders.

    “Drop your shields, if you think asking for advice or help from your investors is showing signs of weakness you have it all wrong. Your investors are by definition already on your side and any problem you are facing or any area of growth where you think they may be able to contribute to or connect you to someone who can be helpful, go for it. I want leaders to ask me ‘what am I doing wrong, where can I level up?’” Reed Sturtevant, The Engine

  • Beyond headcount and budgets, investors with experience leading teams at scale can be very helpful with how to think about organizational design through various stages of growth. Investors can also have a really good sense of leveling across organizations and have seen a lot of creative approaches used across companies.

Financials

Table Stakes:

  • Investment checks
  • Future rounds  —  financing strategy, valuation, etc.

Beyond the Basics:

  • It’s never too soon to get “budget religion”, especially if you have a capital-intensive business where you need to figure out working capital, financing with manufacturing, etc.. Ask for guidance on how best to manage your funds as well as how to track burn and prepare data for future financing to make the diligence process easier for new investors. They may even have models or frameworks other portfolio companies use that you can borrow.
  • Not sure whether your compensation packages are competitive or fair? Or how to think about equity vs. salary splits? Comping your sales team? Your investors have probably seen many different configurations and can help you get creative if you’re trying to land a key hire or to retain and motivate your current team.
  • Other financial areas where investors can be helpful are ways to think about marketing spend as a ratio of investment in engineering or sales/revenue, pricing models and tax considerations.

In all of the above cases, if your investors can’t help you directly, odds are very high that they know someone who can. Good investors won’t expect you, especially if you are a first-time founder, to figure it out all by yourself. For me personally, I always appreciate the humility that comes from anyone who knows what they don’t know and asks for help. It is impossible for anyone to know everything!

How To Ask

There are three ways I think every founder should interact with their investors outside of board meetings (if you have them).

  1. Investor update emails are always a good vehicle for asks. If you’re not sure if anyone on the investment team can be helpful, be specific: “Looking for advice on digital marketing strategies.” or “Would love to talk with someone in your network who can advise my team on HIPPA compliance.”.
  2. Routine 1:1 calls or meetings are a must. This establishes a good touchpoint with investors to establish a rapport and catch up informally instead of waiting for a crisis or issue to arise as a reason for a call. I suggest you always have at least one ask for these meetings and always follow up with a quick email with that ask in writing.
  3. Identify at least one domain area where each investor may serve you best (e.g., I am usually the go-to person for product & engineering or organizational planning for my angel investments and advisees). When the needs arise, set up face-time to dig into that specific topic with that investor.

Remember, your investors are not just here to provide cash. They are invested in you and your company’s success. As Jason Seats of TechStars says, when in doubt, “pretend that they are not an investor and figure out what you’d ask them. If you can’t come up with anything, they may not be a good investor for you.” This can also be a nice hack around targeting the right investors from the start.

Have other examples of ways your investors have been helpful beyond their funds? Please share in the comments.

 

Go Big, Or Go…Startup

big Fish Little Fish

Image source unknown

A common career advice question I get all the time is what the tradeoffs are between going to a startup vs. going to a big company. There are many things to consider and lots of “it depends” when it comes to where you are in your career, where you live etc., but when it comes to the general aspects of a startup vs. mature company, most of the situations don’t vary that much. I’ve done both, several times, so here’s a perspective on the tradeoffs based on my own experiences.

Startup vs. Mature Company

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(c) 2018 Julia B Austin

Putting aside for a moment industry and how you feel about the products the company is building (both of which are very important!), most of the differences between a startup vs. a mature company are pretty obvious. In a mature company, you will likely have more role models to learn from and stronger teams to collaborate with, a clear direction and a mature board. The role you consider may have a narrow scope, but could offer deeper learning and of course great benefits, compensation, etc.. You’ll also get exposure to what good (or bad) looks like at scale and possibly a nice brand for your resume.

Startups can offer a chance to do “all the things” which can be either a blessing or a curse depending on your interests. You may miss out on having peers to collaborate with, have to look outside of your company for mentors and role models or have limited budget to get stuff done, but you may get high value equity in exchange for lower than market-level pay. If you want to dig more into deciding which startup to join, I suggest Jeff Bussgang’s book Entering Startupland which goes deep on the different roles at startups and how to get your foot in the door.

Leadership

One thing often overlooked when considering a new job is the leadership of the company. Serial entrepreneurs will have a very different approach than someone who has limited real-world experience and mature company executive teams can be world class or “legacy” leaders who can’t move with the times. There are many tradeoffs when factoring in leadership into the decision process of startup vs. a mature company.

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(c) 2018 Julia B Austin

Startup founded by serial entrepreneurs: This can often be the best case scenario if you want to learn from those who have “seen the movie before”. They likely had no issue raising money and were selective on who their investors were and who sits on their board. They will know how to get the flywheel moving incited by past mistakes OR failures.

“When I started my fifth company I knew exactly how I wanted to build the team. So, on day one I hired a head of recruiting to get things off to a strong start. I also knew market adoption would be critical to fundraising so focused on growth very early on – before we even had a product!” – David Cancel, CEO & Co-Founder Drift

Serial entrepreneurs may also try to overcorrect in areas where they failed the first time, such as over analyzing or delaying decisions, being too conservative on cash flow or focusing too much on scalability too early in the product development process. If you’re interviewing with a serial entrepreneur, it’s always good to ask what lessons they learned in their last startup and how they’re bringing those lessons into their new venture.

“I joined Drift in part because I wanted to learn from the experience of the co-founders. They’ve seen it before so they anticipate issues, they know when (and how) to hire experts to level up the team, and they know what’s “normal” for a hypergrowth company. It’s the best of both worlds: you get the rollercoaster startup experience with some of the more measured leadership and strategic characteristics of a bigger company.” – Maggie Crowley, Product Manager Drift

Industry veterans doing their first startup: Founders coming from mature companies with no startup experience can have big company confidence, be great at hiring and leading teams, but lack scrappiness to get a Minimum Viable Product (MVP) out the door and work towards product market fit.

“At our first startup after a series of roles at large enterprise software companies, we tried to force a big company perspective on how we did employee feedback and reviews. We were too structured with this initially and quickly cut back to a more loose feedback and review process with our team.” Izzy Azeri & Dan Belcher, Co-Founders Mabl

They may also be too used to having teams of people and systems in place to cover the more mundane duties of running a company and don’t want to get their hands dirty. On the flip side, they often know how to implement those processes and know the people to hire to run them so once the flywheel is moving and cash is in-hand, they can get momentum quickly.

“Earlier in my career, I hired a small team within a large corporation that was scrappy and had entrepreneurial mentality. At my startup, I quickly realized the benefit of once having a corporation behind me when things weren’t working out. The impact of a bad decision or process was much greater with no safety net.” – Karen Young, CEO & Founder Oui Shave

Startup with limited leadership experience: Working with a skilled group of founders leading teams for the first time can be tons of fun. If you bring some experience to the table, it can be very gratifying to not only work from the ground up, but also work alongside these founders as they grow. However, it can be frustrating if you find yourself figuring out things on your own because there’s no one in the company to mentor you. These situations can be very rewarding if you’re patient and you can always get outside mentors and advisors if they’re not available at this type of startup.

“When we started, we got a lot of advice like: stay focused, don’t expand too quickly, be careful that experienced hires match your culture.  All good advice, but we discovered there’s no real substitute for learning the hard way. The lesson just doesn’t sink in until you feel the pain of doing it wrong.” Wombi Rose, CEO & Co-Founder LovePop

Mature company with inexperienced leadership: If they made it this far, they are either wicked smart, lucky or both! More likely they also have surrounded themselves with strong, experienced leaders, investors and/or board members. You can learn a lot from joining a company like this, but they are very, very rare! When companies scale too fast, they can also suffer from having people in roles that have outgrown their experience. Read more about the impact of Hypergrowth situations written by my friend at Reboot, Khalid Halim, for First Round.

Mature companies with experienced leadership: These organizations have all the standard things you’d expect. Probably more politics and process than you’d ever find at a startup, but the benefit of exposure to great role models and best practices can be invaluable. Sometimes, these bigger companies can also expose you to the “dark side” of leadership and processes which are also great learnings on what not to do in your next job or company you may start yourself.

Which comes first in your journey?

For those doing early career path planning and knowing they want to do both a startup and a mature company at some point, there’s always the question of which should come first. Hiring managers at early stage companies can get “spooked” when they see someone with too much time (5+ years) at mature companies; questioning whether the candidate will be able to transition to startup life. Not that it’s impossible, but it’s something to consider. For these candidates, I suggest highlighting any scrappy “ground zero” work they may have done at their companies to demonstrate they can handle ambiguity and take risks. I am also a huge (and very biased) fan of people who’ve joined companies early and scaled with them. They have learned a TON from those experiences and can often start scrappy, but know how to operate at scale. Win-win.

Conversely, someone with a lot of startup experience may have a hard time adjusting to mature company. A hiring manager at a mature company may question whether a candidate with only startup experience can handle a slower pace or won’t know how to navigate a complex organizational structure that requires political and communication savvy. You may have to sacrifice title and maybe some salary to get a foot into larger institutions who may view your past role, which may have been very senior at a startup, to being pretty junior if those around you have decades more experience. However, I always find those with startup experience can be invaluable to a team that needs to be shaken up, take more risks or explore new ground. Often, those who sacrifice title and pay when they joined, make it up fast as they move up the chain in a larger organization.

There’s no right or wrong place to start. A lot depends on how you define your skills and how willing and patient you are in either case to adjust. Much can depend on who hires you and their management philosophy. I’ve seen some people bounce between both types of situations over and over, some that just can’t handle startup life, and others who have startups in their DNA and should just stick with that world 🙂

“At a startup, every job matters and you can see almost daily that you are creating something that wasn’t there before. You have the ability to learn quickly and have a fast feedback loop to let you know how you’re doing. It’s very different working at an established company vs a startup, but you can learn a lot at both – you’ll just learn very different things.” – Rebecca Liebman, CEO & Co-Founder LearnLux

Questions To Ask

Regardless of whether you are a seasoned veteran or fresh out of school, as you ponder whether you want to join a startup or a mature company here are some final things to consider:

  • What tools do you want to add to your toolbox? Will the role allow you to hone skills you already have or add new ones?
  • Who do you want to learn from, and how do you want to learn? You can learn from experienced colleagues and mentors, but having bad role models can also teach you a lot about what not to do. Similarly, if you are an experienced hire coming into a company started by inexperienced founders, you may want to learn by mentoring or teaching these young leaders. Taking the skills you’ve developed over your career and applying them to a new situation in itself can be a very enlightening experience.
  • Who do you want to work with? How important is the size and culture of the team you’ll work with? Remember, you’ll probably spend more waking hours of the day with these people than anyone else in your life – regardless of the size and nature of the company you join.
  • What do you value? At the end of the day, love what you do and decide what role will allow you to maintain the integrity of who you are and who you aspire to be!

Do you have other tips on how to decide whether to join a startup vs. a mature company? Please share in the comments!

What Made You, You

Let’s face it, last year was rough. Rough for our country, rough for story tellers exposing the truths no one wanted to hear and rough for the world we live in as we continue to face climate change, war, poverty, etc. Not to mention suffering through several tough Mercury in retrograde transitions! I had a particularly challenging year myself – personally and professionally – and was ecstatic to put 2017 behind me.

But just like our current president is SO BAD that our country is working towards finding its democratic voice again, and the stories that have been told (and will continue to be told #metoo) are teaching us to listen and act, we each face challenges that can transform who we are. These challenges inevitably make us, us – good, bad or perhaps just more enlightened. This became very apparent to me in 2017.

What made me, me….

Just over a year ago, a work colleague and I were hanging out in the office chatting about life. It was pretty routine for us to wrap up an intense week by unwinding with a short glass of whiskey and story telling. It was a great way for us to continue to foster the strong working relationship we had developed. After over a year of this routine, we had gotten to know each other pretty well and trusted each other to tell some very personal stories about our lives, families and hopes of the future.

That particular evening, I shared a story about something I experienced at a retreat I had recently attended. I won’t get into all the details about the experience, but the short story was that during one of the group sessions at the retreat, I had decided to let go of a toxic relationship with someone in my immediate family(*). I have always carried guilt, sadness and anger about that relationship  – hoping some day it would be different, but knowing in my soul that it would never be what I hoped for nor could I forgive for things said and done. The exercise at the retreat was to let go of something that no longer served us. At that time, I felt that the relationship with that family member no longer served me. (there was a burning ceremony…. it was super intense…)

I shared that experience with my colleague and his immediate response was “you must forgive that person and maintain that relationship because they made you, you.”. I was a little annoyed with that response because I was so damn proud of myself for letting go of a bad relationship that no longer served me, but he continued to push me to consider how even the negative aspects of that relationship undoubtedly had a positive impact on me (motivated me to improve my relationships with other members of my family, developed some of my better traits which were the weaker traits of this family member, etc.). It was pretty profound and hard to argue with.

Even though the conversation that evening was very impactful, it didn’t immediately change my mind and cause me to call the family member up the next day to forgive them. However, the conversation stuck with me. That person, no matter how toxic the relationship was, made me, me. It’s been echoing in my head ever since that conversation with my colleague.

In the past few months, I have created some space in my life to allow me to revisit this topic and consider how this family member made me, me. I have been made aware from other family members that this family member is suffering from age-related health and financial issues and lacks a good support system. They live in a subsidized housing facility with very little access to in-house services or transportation for services elsewhere. While I don’t have unlimited resources, I decided I could help this person have a more comfortable end of life then they would otherwise enjoy. It’s been a huge emotional leap for me to move forward and have compassion for this person and appreciate how they contributed to making me, me. I have also done some family research to develop a deeper understanding of what made them, them and have far more empathy for this person than I have ever had.

We’ve still got a ways to go to figure out how to forge a better, more positive, relationship, but I am confident I am moving in the right direction and both of us will be better for it. I am helping to arrange for better housing and services, helping them with health issues (driving to MD appointments, etc.) and I have started to reengage them in my own family’s lives. This, by the way, is also a huge opportunity to serve as a role model for my kids who are keenly aware of the hardships I endured with this family member. It is healthy to forgive.

I am not suggesting you should maintain a relationship with everyone in your life who made you, you. There are certainly some people in your life who truly put you at emotional and/or physical risk and regardless of whether they made you, you, may not be appropriate to restart or be in a relationship with. In my case, there was abuse in the past, but because it was family and I know how to establish boundaries, this one was safe.

So despite everything, I found my silver lining in 2017 and 2018 is looking good! To the colleague who pushed me on this (you know who you are!), thank you. I am forever grateful for having the time and the means to revisit this relationship and make things better while there is still time.

(*) Intentionally keeping this family member generic to protect their privacy.

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Do you have less than positive life experiences that have made you stronger or give more positive experiences to others? Who made you, you? Please share in the comments!