In this episode we answer questions about underperforming employees. If you have a team, some people on that team will underperform. What do you do when that happens? Can you turn them around, or do you have to let them go? We are here to help! In this episode we answer questions including:

• How long should you give an employee to ramp up?
• Why would a top sales person start missing targets?
• What do you do about executives that aren't working full time?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Reminder: this is not legal advice or investment advice.

Q1: How long should you give an employee to ramp up?

An underperforming new hire is not good news. You should be excited about new people joining your company, not concerned!

It is critical to move quickly. For a technical new hire, you want them to at least be pushing code by the 2 week mark. If a new hire hasn’t made you say “wow” in the first 6 weeks, the odds of it working out are not in your favor.

Overall, an 8-12 week ramp up timeline is reasonable, as long as you are seeing the proper early milestones and an acceleration of key contributions. That being said, if it is not working out by as early as the 2 week mark, you need to take action. Remember, the longer you keep someone who isn’t working out, the harder it is for them to explain the gap in their resume. Thus, deciding to part ways early in the process can benefit both your startup and the new hire.

Q2: Why would a top sales person start missing targets?

Start by investigating why they missed their targets. Is there not enough pipeline? Are their close rates low? Figure out if it’s the sales person, the pitch, the process, or another factor.

Interact with the sales person regularly to correct course. Always make sure you are setting clear expectations. Get them a coach. Pair them up with someone doing well. In short, do what you can to intervene, understand the issue, provide support, and get back on the winning path.

Top sales people are in high demand. If it turns out the performance issue is a result of them interviewing elsewhere, evaluate your incentives plan to see if you are creating enough reasons for them to want to stay and keep performing at a high level.

Q3: What do you do about executives that aren't working full time?

First, have a serious conversation about expectations around availability. Second, focus on why people want to stay. Give them reasons to want to work hard! Finally, make sure motivation and engagement is part of your interview process. Hiring motivated self-starters is always in season.

Ultimately, you want underperforming executives to turn the tide and start creating more value for the company. Consider setting more ambitious goals for them. In doing so, you will have a measurable way to see if their output rises to the occasion which, in turn, should result in increasing their work-time presence. Include regular check-ins as part of the process to achieve the goal.

In this episode we answer questions about innovation. Startups are expected to innovate, but what does that mean? What is innovation and how does it become an advantage? We are here to help! In this episode we answer questions including:

• What is innovation?
• Is there a process to innovation?
• What is the cost to not innovating?
• How do I know if I'm being innovative?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Reminder: this is not legal advice or investment advice.

Q0: What is innovation?
Innovation is the process to generate a new method, idea, or product that solves a problem. Innovation is an umbrella term that includes entrepreneurship, corporate innovation, social innovation, and others.

Adoption is key. The intent of innovation is to create a positive impact, not solely come up with new ideas.

Q1: Is there a process to innovation?
Yes! However, innovation is not a direct line process. While there are common paths and milestones, the process requires judgement and the ability to cycle backwards and iterate.

Key steps include:

1. Small teams
2. Be uncomfortable: short deadlines and pressurized situations
3. The common start across every innovation process is to identify “the problem”. Talk to people. Don’t do surveys. You need to find problems people need fixed. When you have done enough user interviews and found a problem, define it with precision.
4. Brainstorm a variety of ways that you can solve the problem.
5. Then, another important “judgement” moment. Amongst all of the possible ways to solve the problem, prioritize one. Figure out the solution that is closest to magic but also plausible to build.
6. Run fast, incremental tests to try to solve part of the problem for your “true believers” – the people who feel the problem strong enough that they are willing to try your v1 solution.
7. Collect data from your tests, iterate, and test again.

Resources available online include content about Human Centered Design, Design Thinking, and more. In fact, two of our hosts have produced tons of fantastic content on the topic: Ash Rust on Medium and Sean Byrnes’ The Breaking Point on Substack.

Q2: What is the cost to not innovating?

The cost for doing nothing can be catastrophic. A PwC survey of more than 4,700 CEOs worldwide showed that “45% of the respondents were worried that their businesses wouldn’t be viable in a decade without reinvention.”

Innovation is a durable skill set.

Innovation is hard to learn, but it is one of the few advantages you have. Innovation is a head start. You won’t win by playing by the rules, you win by creating a new game.

Q3: How do I know if I'm being innovative?

There is no set of rules to guarantee that you are being innovative. Your innovation success hinges upon achieving some level of adoption.

That being said, if you answer “yes” to the following questions, you are on the right track:

• Are you talking to customers, users, and stakeholders to understand where opportunities exist?
• Are you describing problems with precision?
• Are you running fast, incremental tests then iterating on your solutions?

If customers want your product or at least the idea of it, that’s a good sign. Furthermore, if competitors copy your idea, that’s a sign that you are bringing new value to an opportunity.

In this episode we answer questions about startup accelerators. Accelerators are programs that promise to help improve your chances of startup success, but how do they actually work? We are here to help! In this episode we answer questions including:

• What do I get if I join an accelerator?
• How do I know if an accelerator is worth it?
• How do I get the most out of my accelerator?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Reminder: this is not legal advice or investment advice.

Q1: What do I get if I join an accelerator?

Well-established accelerators typically provide:

• Cash: they typically invest. The amount varies and the terms are often on the lower side vs. what you could get from going directly to multiple investors to raise a round.
• Demo Day: the fastest way to 100 investor meetings. Accelerators host a showcase event for their startups and their network of investors to meet. This can be a huge value, helping you to line up investor meetings.
• Network: an accelerator immerses you into a network of fellow founders, investors, and company builders. They can provide mentorship and open doors for leads.
• Tools: accelerators may also provide tools to simplify how you connect with and benefit from the network.
• Healthy competition: working alongside and learning from other ambitious founders is a great way to create some healthy urgency for your startup.
• Serendipity: all of this combines to create new opportunities for you. If you put in the right kind of work, you may be surprised to see what doors open.

Q2: How do I know if an accelerator is worth it?

This is a critical question to ask; there are lots of snake oil salespeople.

Ask yourself what you need first:

• Need help fundraising? YC has shown that a premier accelerator can help with that; however, not every accelerator has shown they can help.
• Need help selling? Some industry or focused accelerators can help teach you.
• Need help recruiting? Some accelerators can help mostly through association with their brand.

Generally, there are cheaper ways to get the help an accelerator offers.

When evaluating the benefits, consider the following value that accelerators can offer:

• Cash: is it at least 6 figures?
• Demo day: are there plenty of examples of recent multi-million dollar rounds from the program?
• Network: are there well known alumni and speakers at their events?
• Tools: do alumni report using their tools?

Make sure the benefits they offer have substance.

Q3: How do I get the most out of my accelerator?

Set expectations with your co-founders about the desired outcome from the accelerator. Is it to accelerate sales? Is it to fundraise? Work backwards from your end goal so that you know where to prioritize your efforts.

Talk to founders that have been through the same accelerator – preferably before applying! Identify what the most successful companies did in the program and make a plan to do those things.

Once in the accelerator:

• Hit the ground running so you’re always at the front of your class.
• Take control of who you work with, rather than waiting for the accelerator to assign mentors.
• Be creative with your tests: your accelerator companions will be eager to help you amplify what you do!

In this episode we answer questions about building your sales team. Many startups sell their product via sales people, and building your sales team is one of the most important things you will do. We are here to help! In this episode we answer questions including:

• How do I hire my first salesperson?
• What is a sales commission plan?
• How do I know if a salesperson is doing well?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Reminder: this is not legal advice or investment advice.

Q1: How do I hire my first salesperson?
To source candidates, consider various hiring platforms, such as Craigslist, Indeed, LinkedIn, ZipRecruiter, and Wellfound. Your network may have fantastic candidates. Ask fellow founders and investors. Check on people you have worked with previously.

To filter and evaluate candidates, start with a project, such as a PowerPoint sales pitch. Filter further via phone interviews, ultimately leading to an onsite.

Ash sparked some serious debate with his recommendation on the final phase of the hiring process! To combat the high attrition rate in sales and to hedge against the difficulty of predicting how well a new hire will work out, he suggested making 3 hires per sales role that you want to fill.

While making 3 hires per sales role may fit your hiring plan, we anticipate that most startups will hire one sales person per role.

Your first sales person will contribute to your startup culture. Set up this new hire for success. Before you hire your first salesperson, make sure you can clearly articulate a few key aspects of your business, such as:

• The problem you solve.
• Your customer profile.
• How your product solves their problem.
• Why current customers value your product.

If you do not know the answers to these questions, you are setting this first sales hire up for failure.

Q2: What is a sales commission plan?
Sales people get paid two ways: salary & commissions. A sales commission plan describes the income a sales person makes based on performance.

A simple example of a sales commission plan is to pay a sales person a % of the deal value that they close (i.e. 10% of all deals).

Companies like sales commission plans because they allow the business to both incentivize and reward performance. A good sales commission plan clearly ties performance to important areas of growth for the business.

The plan you choose is important because it provides specific incentives! Do you want your sales people chasing really big deals? Or should they prioritize a larger volume of little deals? Your sales commission plan can influence priorities.

Q3: How do I know if a salesperson is doing well?
It is hard to distill progress vs. noise. There are steps you can take to add more objectivity to your evaluation process:

• They should immediately shadow you in all deals.
• They should master your pitch in their first week or two.
• They should book lots of calls: ideally 10 a week.
• They should not focus their energy on a small number of marquee leads.
• They should use and update the existing sales playbook vs. going in a new direction.
• They should generate their own pipeline within a month.
• They should own their own deals after a month.
• They should move deals forward in their first quarter.
• If your sales cycle is less than 45 days, they should close their first deal in their first quarter.

Sales people need to be ROI positive, so they should pay for themselves fairly quickly.

In this episode we answer questions about raising money from Venture Capital funds. Many startup companies seek VC funding, but it can be a complex process if you haven't done it before. We are here to help! In this episode we answer questions including:

• Is a SAFE or priced equity round better?
• What's the recommended amount to raise at every stage?
• How do I meet investors to pitch?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Reminder: this is not legal advice or investment advice.

Q1: Is a SAFE or priced equity round better?

There is no right answer that you can apply to every situation. A SAFE is often faster, less complex, and maintains more control for the founders. Because of their simplicity and the flexibility they offer to an unproven startup, SAFEs are a frequent choice for an early-stage startup that is still figuring out much of its business.

However, there are plenty of situations where a priced round makes sense. A priced round can provide more clarity about ownership and the present valuation of the company. However, this clarity adds complexity to the process. In addition to needing to negotiate with more precision about the valuation and ownership, a priced round usually involves a board seat for an investor. Thus, you are forcing your company to grow up a lot right now with a priced round.

Q2: What's the recommended amount to raise at every stage?

Consider raising as little as possible – enough to get to your next milestone so you can raise the next round. Capital is expensive!

While the round size can vary widely from one startup to the next, these are more common amounts that startups raise at key stages:

• Pre-seed - $250-$750k
• Seed - $1-3M
• Series A - $5-10M
• Series B - $15-25M
• Series C - Anything can happen

How do you which stage you are at today? It’s hard to know with complete confidence until you go out and raise!

Q3: How do I meet investors to pitch?

Volume is key when it comes to a successful fundraise. The following avenues are great channels for meeting investors:

• Warm intros from other entrepreneurs is the golden ticket.
• With high quality emails, cold outreach can generate a ~30% response rate.
• Conferences and events.
• Press.
• Customer referrals causing inbound.

Make it easy for people in your network to make warm intros: send an email blurb that they can easily copy and paste. And of course, consistently reach new milestones for your business – don’t forget that part of the equation!

In this episode we answer questions about finding a co-founder and managing your relationship with your co-founder for the road ahead. Co-founder conflict is one of the top reasons for startup failure; many argue it is the primary cause of startup failure in the early days. We are here to help! In this episode we answer questions including:

• How do I find a co-founder?
• Can I add a co-founder later?
• What are the best ways to avoid co-founder conflict?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Q1: How do I find a co-founder?
Best practices include:

1: Build your startup and have conversations with interesting people. Talk to the best people you know in tech and ask who are the best people they know. As you build relationships around the problem you aim to solve or the industry within which your startup operates, you can generate potential co-founder leads.

2: Use your network. Connections from past employers, university mailing lists.

3: Use helpful tools. One such tool is the YC co-founder matching platform.

4: Create opportunities for serendipity. Go to events, compete in hackathons, and spend time learning from others that want to solve meaningful problems.

Finding a co-founder takes time. Build a relationship with a prospective co-founder first, work together on some projects, and confirm compatibility across key areas before rushing into co-founder status.

Q2: Can I add a co-founder later?
Yes! Starting the company yourself and hiring a co-founder is a best practice. "Co-founder" has no formal definition; thus, you can add a co-founder at anytime.

When you add a co-founder later than typical, then you may be able to start the co-founder relationship with more clarity about the direction of the business. For example, you may already have a clear problem you are solving with customers and investors. This can make it easier to identify the complementary skills that you would like to add via a co-founder.

The biggest problem is equity. How much can your co-founder own? The good news is that common vesting schedules help protect you and the company from a co-founder relationship that does not work.

Q3: What are the best ways to avoid co-founder conflict?
Co-founder conflict is common; it is a leading cause of startup death. Expectation setting is the root of all conflict. How do they react under pressure? What about when there is a lot of money on the line?

You can de-risk this process by knowing your co-founder before you start the company.

To align on expectations, be honest and transparent with each other about responsibilities, timelines, and priorities.

It is not reasonable to think that you can create a successful startup by avoiding some executive friction. Growth and obstacles create friction. Set up a good framework for debates and empower decision makers.

It is very rare for co-founding teams to stay together for the 10+ years it takes to bring a great company to life.

In this episode we answer questions about managing your time. Startups are all about speed, so you need to make the most of every hour of every day. We are here to help! In this episode we answer questions including:

• Where should I spend my time as the CEO?
• How often should we have team meetings?
• Is our product development velocity high enough?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Reminder: this is not legal advice or investment advice.

Q1: Where should I spend my time as the CEO?
As your team grows, your responsibilities will shift: less tasks as an individual contributor and more responsibilities to drive the overall company strategy. A classic breakdown of your responsibilities is 30% product, 30% money (sales, fundraising), and 30% HR.

However, if you are growing the team, hiring should be 80% of your time. Convincing great talent to join the company is hard and requires a lot of your focus.

Critical tasks that CEOs often do not spend enough time on include 1on1s, setting goals, and customer success.

In short, your responsibility is to shape the overall vision and the corresponding messaging (within the company and outside of it) and empower the talent on the team.

Q2: How often should we have team meetings?
Startups are not like big companies; you should aim for the fewest possible meetings! Consider 1 to 2 meetings a week to define priorities and assign responsibilities. Inevitably more meetings will come up – focus on doing the work, not talking about the work. Keep meetings to 20 minutes.

By keeping the volume of team meetings low, you can recognize that these are precious synchronous moments. Build a healthy routine (for example, always starting right on time, sending an agenda, or sending action items post-meeting) to maximize their output.

Q3: Is our product development velocity high enough?
If you’re not sure, then it’s likely a problem. Product development velocity should be always increasing. If it’s not, then you aren’t getting the most from your team. You need a combination of authentic urgency (i.e. pushing towards a great milestone for your customers) and a team that can motivate itself.

If velocity is not high enough, the best way to speed things up is cut down the scope of work: remove features and reduce use cases. When you are more narrow with the scope, it’s much easier to move quickly.

If you sense a deeper problem, set very clear goals on short timelines. Often people are ambitious in the goals they set for themselves and, with a short timeline, it will be easier to hold them accountable. If someone or more than 1 person isn’t working out, you may need to let them go.

In this episode we answer questions about complex exit options. While we all hope for a bit exit, startups more often face complex and difficult exit options including low sale prices, mergers and wind downs. We are here to help! In this episode we answer questions including:

• What happens if my investors want to sell but I don't?
• Is a merger ever a good idea?
• How do I know it's time to shut down my company?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Reminder: this is not legal advice or investment advice.

Q1: What happens if my investors want to sell but I don't?
In most cases, it’s the primary founder’s decision. Facebook was pushed to sell to Yahoo! but refused. However, there are often consequences for refusing to accept an acquisition offer. Those consequences include executive resignations, investors deciding to no longer fund subsequent rounds, and a hostile board.

If you are OK with those consequences, you are ready to keep pushing.

Much of this decision rests on how much conviction you have about the next stage of growth for your startup. How much runway remains? Is your startup growing? Do you have any signal that suggests you are reaching an inflection point? Is your team uniquely positioned to succeed with this opportunity vs. pursuing a new opportunity? These are the types of questions to answer when deciding to accept or turn down an acquisition offer of this sort.

Q2: Is a merger ever a good idea?
Mergers are very risky. There are integration costs, culture clashes, and a mix of incentives. If you and your competitor are the two clear leaders, it can mean 1+1=10. However, if you are just two players in a sea of competition, pursuing a merger may distract you.

A merger may make the most sense as a last resort. If you cannot sell your startup and are going out of business, a merger can be the life raft. A merger can save some of the employees’ jobs and investor stakes. This last resort is worth a shot, but expect a low probability of a good outcome.

Finally, if you decide to pursue a merger, expect the merger integration to take at least a year. Manage your risk and plan accordingly!

Q3: How do I know it's time to shut down my company?
If you are out of cash, it’s an easy decision. If not, it’s a really hard decision with no clear answer. Some people waste years of their life on a dying company, while others find a breakthrough at the end and become a big win.

Is there something else you would rather do with your time? Are you and your team members uniquely positioned to pursue another opportunity instead?

While there is no definitive process for this decision, consider the following: give yourself a clear timeline with objective goals. These goals should likely focus on demand, customers landed, or revenue received. With this data in hand: do you have enough evidence to justify working on this further vs. shutting down so that you can allocate your time elsewhere? This comes down to opportunity cost, the realities of how much cash remains for your startup, and how your gut evaluates your options.